105-95-3

Basic information

• Product Name: Ethylene brassylate
• Synonyms: Cyclic ethylenetridecanedioate;Emeressence 1150;1,4-Dioxacycloheptadecane-5,17-dione;Musk T;NSC 46155;Tridecanedioicacid, cyclic ethylene ester (7CI,8CI);Ethylene glycol, cyclic tridecanedioate(8CI);Astratone;Cyclic ethylene glycol tridecanedioate
• CAS NO: 105-95-3
• Molecular Formula: C₁₅H₂₆O₄
• Molecular Weight: 256.338
• EINECS: 203-347-8
• Product Categories: Alphabetical Listings;E-F;Flavors and Fragrances;Water treatment chemicals;Flavor;As an aroma chemical for use in flavor, fragrance, and other applications
• Mol File: 105-95-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: -8 °C
• Boiling Point: 476.1 °C at 760 mmHg
• Flash Point: 243.9 °C
• Appearance: colorless transparent liquid
• Density: 0.977 g/cm³
• Vapor Pressure: 8.34E-09mmHg at 25°C
• Refractive Index: 1.438
• Water Solubility: 14.8mg/L at 20℃
• CAS DataBase Reference: Ethylene brassylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethylene brassylate(105-95-3)
• EPA Substance Registry System: Ethylene brassylate(105-95-3)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R38:
• Safety Statements: S26:; S36:
• WGK Germany: 2
• RTECS: YQ1927500
• Hazardous Substances Data: 105-95-3(Hazardous Substances Data)

Usage

Description

Ethylene brassylate, also known as macrocyclic compound, is an artificial fragrance material derived from the depolymerization of the corresponding polyester. It is characterized by its musk-like odor and sweet, slightly fatty taste. Ethylene brassylate is a colorless to pale yellow transparent liquid and has not been reported to occur naturally.

Uses

Used in Fragrance Industry:
Ethylene brassylate is used as a fragrance ingredient for its musk-like odor and sweet taste. It is particularly valued for its ability to enhance the overall scent profile of various products, such as perfumes, colognes, and other personal care items.
Used in Flavor Industry:
Ethylene brassylate is also used in the flavor industry to impart a musky, sweet, powdery, floral, vanilla, and perfumey taste to food and beverage products. Its unique taste characteristics make it a valuable addition to the flavorist's toolbox.
Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care industry, ethylene brassylate is used as an additive to provide a pleasant and long-lasting scent to products such as lotions, creams, and shampoos. Its musk-like odor and sweet taste make it an ideal choice for enhancing the sensory experience of these products.
Used in Cleaning and Home Care Products:
Ethylene brassylate is also utilized in the formulation of cleaning and home care products, such as detergents, fabric softeners, and air fresheners. Its ability to provide a musk-like scent and sweet taste makes it a popular choice for creating a pleasant and inviting atmosphere in the home.

Preparation

By esterification of brassylic acid.

Flammability and Explosibility

Nonflammable

Trade name

Musk T? (Takasago), MC-5 (Soda Aromatic)

InChI:InChI=1/C14H24O4/c15-13-10-8-6-4-2-1-3-5-7-9-11-14(16)18-12-17-13/h1-12H2

Synthetic route

brassylic acid (505-52-2) → 1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3)

Conditions	Yield
With ethylene glycol at 200℃; under 2 Torr; Erhitzen des Reaktionsprodukts mit wenig Zinn(II)-chlorid-dihydrat unter 1 Torr auf 270grad;

brassylic acid (505-52-2) + ethylene glycol (107-21-1) → 1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 10h;	189 mg

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 1,13-tridecanediol (13362-52-2)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 3.5h; Ambient temperature;	98%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; Reflux;	76%
With lithium aluminium tetrahydride In diethyl ether Reflux;

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → poly[-CO(CH2)11CO(CH2)2O-]

Conditions	Yield
Candida antarctica lipase at 75℃; for 24h; Polymerization; ring cleavage;

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 13-bromo-1-tridecylalcohol (116754-58-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 0 - 20 °C / Reflux 2: hydrogen bromide / water; toluene / 22 h / Dean-Stark; Reflux View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (Z)-14-tricosen-1-ol (50995-26-1)

Conditions

Yield

Multi-step reaction with 7 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → heptadec-16-yn-1-ol (62873-30-7)

Conditions

Yield

Multi-step reaction with 7 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 2-((13-bromotridecyl)oxy)tetrahydro-2H-pyran (116452-12-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / diethyl ether / Reflux 2: hydrogen bromide / toluene / Reflux; Dean-Stark 3: pyridinium p-toluenesulfonate / dichloromethane / 20 °C View Scheme
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 0 - 20 °C / Reflux 2: hydrogen bromide / water; toluene / 22 h / Dean-Stark; Reflux 3: pyridinium p-toluenesulfonate / dichloromethane / 18 h / 20 °C View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 14-heptadecyn-1-ol (159627-68-6)

Conditions

Yield

Multi-step reaction with 6 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 14-tricosyn-1-ol (159627-64-2)

Conditions

Yield

Multi-step reaction with 6 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (Z)-14-tricosenyl bromide (159627-66-4)

Conditions

Yield

Multi-step reaction with 9 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 8: 98 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature 9: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 1-tetrahydropyranyloxy-14-pentadecyne (159627-62-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 16-tetracosyn-1-ol (159627-71-1)

Conditions

Yield

Multi-step reaction with 10 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (Z)-16-tetracosen-1-ol (159627-72-2)

Conditions

Yield

Multi-step reaction with 11 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 11: 93 percent / H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (Z)-16-tetracosenyl bromide (159627-74-4)

Conditions

Yield

Multi-step reaction with 13 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 11: 93 percent / H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 12: 95 percent / Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 13: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 2-(heptadec-16-yn-1-yloxy)tetrahydro-2H-pyran (159627-69-7)

Conditions

Yield

Multi-step reaction with 8 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 1-tetrahydropyranyloxy-14-heptadecyne (159627-67-5)

Conditions

Yield

Multi-step reaction with 5 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (2S,3R,18Z)-2,3-epoxy-18-heptacosen-1-ol (159627-82-4)

Conditions

Yield

Multi-step reaction with 11 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 8: 98 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature 9: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 10: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h 11: 95 percent / 1M tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (2S,3R,20Z)-2,3-epoxy-20-octacosen-1-ol (159627-77-7)

Conditions

Yield

Multi-step reaction with 15 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 11: 93 percent / H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 12: 95 percent / Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 13: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 14: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h 15: 94 percent / 1M tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 1-tetrahydropyranyloxy-14-tricosyne (159627-63-1)

Conditions

Yield

Multi-step reaction with 5 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → 1-tetrahydropyranyloxy-16-tetracosyne (159627-70-0)

Conditions

Yield

Multi-step reaction with 9 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (Z)-14-tricosenyl tosylate (159627-65-3)

Conditions

Yield

Multi-step reaction with 8 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 8: 98 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (Z)-16-tetracosenyl tosylate (159627-73-3)

Conditions

Yield

Multi-step reaction with 12 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 11: 93 percent / H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 12: 95 percent / Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (2S,3R,18Z)-2,3-epoxy-18-heptacosenyl tosylate

Conditions

Yield

Multi-step reaction with 12 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 8: 98 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature 9: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 10: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h 11: 95 percent / 1M tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C 12: 99 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (2S,3R,20Z)-2,3-epoxy-20-octacosenyl tosylate

Conditions

Yield

Multi-step reaction with 16 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 11: 93 percent / H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 12: 95 percent / Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 13: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 14: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h 15: 94 percent / 1M tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C 16: 99 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (2S,3R,18Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-18-heptacosene (159627-81-3)

Conditions

Yield

Multi-step reaction with 10 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 8: 98 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature 9: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 10: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene (159627-76-6)

Conditions

Yield

Multi-step reaction with 14 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 11: 93 percent / H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 12: 95 percent / Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 13: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 14: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (E)-14-tricosen-1-ol

Conditions

Yield

Multi-step reaction with 7 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (9Z,25R,26S,43Z)-25,26-epoxy-9,43-henpentacontadiene

Conditions	Yield
Multi-step reaction with 14 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 11: 93 percent / H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 12: 95 percent / Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 13: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 14: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2.5 h, 2.) ether, HMPA, r.t., 6 h View Scheme
Multi-step reaction with 13 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 8: 98 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature 9: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 10: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h 11: 95 percent / 1M tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C 12: 99 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 1.5 h / Ambient temperature 13: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2.5 h, 2.) ether, HMPA, r.t., 6 h View Scheme

1,4-dioxa-cycloheptadecane-5,17-dione (105-95-3) → (9Z,25S,26R,43Z)-25,26-epoxy-9,43-henpentacontadiene

Conditions	Yield
Multi-step reaction with 17 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature 8: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 9: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 10: 94 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 11: 93 percent / H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 12: 95 percent / Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 13: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 14: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2 h, 2.) ether, HMPA, r.t., 18 h 15: 94 percent / 1M tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C 16: 99 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 1.5 h / Ambient temperature 17: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2.5 h, 2.) ether, HMPA, r.t., 6 h View Scheme
Multi-step reaction with 10 steps 1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 93 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: H2, quinoline / Lindlar palladium catalyst / hexane / 20.5 h / Ambient temperature 8: 98 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature 9: 97 percent / LiBr, NaHCO3 / acetone / 15 h / Ambient temperature 10: 1.) Mg, 2.) CuI / 1.) ether, r.t., 2.5 h, 2.) ether, HMPA, r.t., 6 h View Scheme

Upstream product

• 505-52-2 brassylic acid 
• 107-21-1 ethylene glycol 

Downstream Products

• 13362-52-2 1,13-tridecanediol 
• 116754-58-6 13-bromo-1-tridecylalcohol 
• 50995-26-1 (Z)-14-tricosen-1-ol 
• 159627-65-3 (Z)-14-tricosenyl tosylate 
• 159627-73-3 (Z)-16-tetracosenyl tosylate 
• 159627-81-3 (2S,3R,18Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-18-heptacosene 
• 159627-76-6 (2S,3R,20Z)-1-tert-butyldiphenylsilyloxy-2,3-epoxy-20-octacosene 
• 1193721-67-3 22,22,22-d₃-docosanoic acid 

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Copolymerization of Ethylene brassylate (cas 105-95-3) with δ-valerolactone towards isodimorphic random copolyesters with continuously tunable mechanical properties08/15/2019

Ring opening copolymerization of ethylene brassylate (EB) and δ-valerolactone (δ-VL) with various feeding ratios catalyzed by triphenyl bismuth was performed to prepare poly(ethylene brassylate-co-δ-valerolactone) copolyesters. The reactivity ratios of EB and δ-VL were firstly determined to ...detailed

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Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group**

Macrolactones constitute a privileged class of natural and synthetic products with a broad range of applications in the fine chemicals and pharmaceutical industry. Despite all the progress made towards their synthesis, notably from seco-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables a convenient access to macrolactones, macrodiolides and esters with a broad versatility. Kinetic studies and DFT computations were performed to rationalize the reactivity of the pentafluorophenyl group in macrolactonization reactions.