162358-05-6

Basic information

• Product Name: 2-(4-OCTYLPHENYL)ETHANOL
• Synonyms: 2-(4-OCTYLPHENYL)ETHANOL;Benzeneethanol, 4-octyl;4-Octyl-benzeneethanol;4-Octylphenethyl alcohol
• CAS NO: 162358-05-6
• Molecular Formula: C₁₆H₂₆O
• Molecular Weight: 234.37704
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 162358-05-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 306.3±10.0℃ (760 Torr)
• Flash Point: 116.2±4.2℃
• Appearance: /
• Density: 0.931±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate, Hexane
• PKA: 14.92±0.10(Predicted)
• CAS DataBase Reference: 2-(4-OCTYLPHENYL)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-OCTYLPHENYL)ETHANOL(162358-05-6)
• EPA Substance Registry System: 2-(4-OCTYLPHENYL)ETHANOL(162358-05-6)

Safety Data

• Hazardous Substances Data: 162358-05-6(Hazardous Substances Data)

Usage

Description

2-(4-Octylphenyl)ethanol, with the CAS number 162358-05-6, is an organic compound characterized by its oily texture. It is primarily utilized in the field of organic synthesis, where its unique chemical properties contribute to the creation of various complex molecules and structures.

Uses

Used in Organic Synthesis:
2-(4-Octylphenyl)ethanol is used as a synthetic building block for the development of more complex organic compounds. Its oily nature and compatibility with a range of chemical reactions make it a valuable component in the synthesis of various organic molecules.
Used in Chemical Industry:
In the chemical industry, 2-(4-Octylphenyl)ethanol is employed as an intermediate in the production of specialty chemicals, pharmaceuticals, and other advanced materials. Its unique structure and properties allow for the creation of novel compounds with specific applications and functions.
Used in Pharmaceutical Industry:
2-(4-Octylphenyl)ethanol may also find application in the pharmaceutical industry, where it can be used as a starting material for the synthesis of new drugs or as a component in the formulation of existing medications. Its versatility in organic synthesis makes it a promising candidate for the development of innovative pharmaceutical products.

InChI:InChI=1S/C16H26O/c1-2-3-4-5-6-7-8-15-9-11-16(12-10-15)13-14-17/h9-12,17H,2-8,13-14H2,1H3

Synthetic route

2-(4-(oct-1-yn-1-yl)phenyl)-1-ethanol → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 17h;	98%

acetic acid 2-(4-octylphenyl)ethyl ester (162358-04-5) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
With sodium methylate In methanol at 20℃; for 8h;	93%
With sodium methylate In methanol for 6h; Reflux;	92%
With sodium methylate In methanol for 6h; Reflux;	92%

1-bromo-octane (111-83-1) + C28H25BrO → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Stage #1: 1-bromo-octane With iodine; magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: C28H25BrO With pyridine; dmap; sodium hydroxide Heating; Stage #3: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 120℃; for 4h;	80%

1-bromo-octane (111-83-1) + 4-(2-hydroxyethyl)benzyl bromide (96044-43-8) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Stage #1: 1-bromo-octane With iodine; magnesium In diethyl ether for 1h; Inert atmosphere; Reflux; Stage #2: 4-(2-hydroxyethyl)benzyl bromide With sodium hydroxide In tetrahydrofuran at 110℃; for 4h; Temperature;	75%

octylmagnesium bromide (17049-49-9) + acetic acid 2-[4-(trifluoromethanesulfonyloxy)phenyl]ethyl ester (712223-57-9) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6) + acetic acid 2-(4-octylphenyl)ethyl ester (162358-04-5)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate In tetrahydrofuran for 1h;	A 20% B 64%

1-Chlorooctane (111-85-3) + 4-(2-hydroxyethyl)benzyl bromide (96044-43-8) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Stage #1: n-chlorooctane With iodine; magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: 4-(2-hydroxyethyl)benzyl bromide With sodium hydroxide In tetrahydrofuran at 120℃; for 4h;	20%

p-hydroxyphenethyl alcohol (501-94-0) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / NaHSO4 on silica / hexane / 26 h / Heating 2: 94 percent / pyridine / CH2Cl2 / 1 h / 20 °C 3: 20 percent / Fe(acac)3; NMP / tetrahydrofuran / 1 h View Scheme

2-(4-hydroxyphenyl)ethyl acetate (58556-55-1) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / pyridine / CH2Cl2 / 1 h / 20 °C 2: 20 percent / Fe(acac)3; NMP / tetrahydrofuran / 1 h View Scheme

n-octanoic acid chloride (111-64-8) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 43 percent / AlCl3 / 1,2-dichloro-ethane / 3 h / 20 °C 2: triethylsilane; TFA / 1,2-dichloro-ethane / 3 h / 20 °C 3: 3.40 g / NaOMe; MeOH / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1,2-dichloro-ethane / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: trifluoroacetic acid; triethylsilane / 3 h / 20 °C 3.1: sodium methylate / methanol / 6 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1,2-dichloro-ethane / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: trifluoroacetic acid; triethylsilane / 3 h / 20 °C 3.1: sodium methylate / methanol / 6 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride / 1,2-dichloro-ethane / 0 - 20 °C 2: triethylsilane; trifluoroacetic acid / 20 °C 3: sodium methylate / methanol / 3 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / 0.01 h / 0.25 - 0.3 °C 1.2: 0 h / 0.2 - 0.5 °C 2.1: sodium hydroxide / water; methanol / 1.5 h / 0.1 - 0.3 °C 3.1: palladium 10% on activated carbon; hydrogen / 0 h / 0.4 °C / Autoclave 4.1: sodium hydroxide / water; methanol / 0.2 - 0.3 °C View Scheme

acetic acid phenethyl ester (103-45-7) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 43 percent / AlCl3 / 1,2-dichloro-ethane / 3 h / 20 °C 2: triethylsilane; TFA / 1,2-dichloro-ethane / 3 h / 20 °C 3: 3.40 g / NaOMe; MeOH / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1,2-dichloro-ethane / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: trifluoroacetic acid; triethylsilane / 3 h / 20 °C 3.1: sodium methylate / methanol / 6 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1,2-dichloro-ethane / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: trifluoroacetic acid; triethylsilane / 3 h / 20 °C 3.1: sodium methylate / methanol / 6 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / 0.01 h / 0.25 - 0.3 °C 1.2: 0 h / 0.2 - 0.5 °C 2.1: sodium hydroxide / water; methanol / 1.5 h / 0.1 - 0.3 °C 3.1: palladium 10% on activated carbon; hydrogen / 0 h / 0.4 °C / Autoclave 4.1: sodium hydroxide / water; methanol / 0.2 - 0.3 °C View Scheme

2-(4-octanoylphenyl)ethyl acetate (162358-03-4) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylsilane; TFA / 1,2-dichloro-ethane / 3 h / 20 °C 2: 3.40 g / NaOMe; MeOH / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: trifluoroacetic acid; triethylsilane / 3 h / 20 °C 2: sodium methylate / methanol / 6 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: trifluoroacetic acid; triethylsilane / 3 h / 20 °C 2: sodium methylate / methanol / 6 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: triethylsilane; trifluoroacetic acid / 20 °C 2: sodium methylate / methanol / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / water; methanol / 1.5 h / 0.1 - 0.3 °C 2: palladium 10% on activated carbon; hydrogen / 0 h / 0.4 °C / Autoclave 3: sodium hydroxide / water; methanol / 0.2 - 0.3 °C View Scheme

4-iodophenethyl alcohol (52914-23-5) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / 17 h / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 17 h / 20 °C View Scheme

n-octyne (629-05-0) → 2-(4-Octylphenyl)ethyl alcohol (162358-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / 17 h / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 17 h / 20 °C View Scheme

methanesulfonyl chloride (124-63-0) + 2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 4-octylphenethyl methanesulfonate (162358-06-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 5h;	95%
With triethylamine In dichloromethane at 20℃; for 5h;	95%
With triethylamine In dichloromethane for 1h;

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate (162358-08-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Et3N / CH2Cl2 / 1 h 2.1: 5.37 g / LiI / tetrahydrofuran / 4 h / 20 °C 3.1: NaH / dimethylformamide / 30 h 3.2: 82 percent / dimethylformamide / 1 h / 50 - 60 °C View Scheme
Multi-step reaction with 3 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 3.2: 61 percent / ethanol / 3 h / 65 °C View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.5 h 1.2: 3 h / 0 - 20 °C 2.1: sodium iodide / tetrahydrofuran / 20 °C 3.1: caesium carbonate / dimethyl sulfoxide / 3 h / 60 °C / Inert atmosphere 3.2: 60 - 80 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium iodide / butanone / 0.67 h / 0.8 - 0.85 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0.45 - 0.5 °C / Inert atmosphere 2.2: 0.4 - 0.45 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 30 °C / Inert atmosphere 2: tetra-(n-butyl)ammonium iodide; sodium iodide / 3 h / Inert atmosphere 3: tetra-(n-butyl)ammonium iodide; caesium carbonate / dimethyl sulfoxide / 25 - 85 °C / Inert atmosphere View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 1 h 2: 5.37 g / LiI / tetrahydrofuran / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 1 h / 20 °C 2: 16.0 g / NaI / butan-2-one / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.5 h 1.2: 3 h / 0 - 20 °C 2.1: sodium iodide / tetrahydrofuran / 20 °C View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → fingolimod (162359-55-9)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 3.2: 61 percent / ethanol / 3 h / 65 °C 4.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 5.1: 8.25 g / pyridine / 16 h / 20 °C 6.1: 2 N aq. LiOH / methanol / 2 h / Heating View Scheme
Multi-step reaction with 4 steps 1.1: sodium iodide / butanone / 0.67 h / 0.8 - 0.85 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0.45 - 0.5 °C / Inert atmosphere 2.2: 0.4 - 0.45 °C / Inert atmosphere 3.1: calcium chloride / water; isopropyl alcohol / 0 h / 0.2 - 0.3 °C 3.2: 0.01 h / 0 - 0.5 °C 3.3: 0 h / 0.15 - 0.5 °C 4.1: sodium hydroxide / water; methanol / 2 h / Reflux View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 2-amino-2-hydroxymethyl-4-(4-octyl-phenyl)-butyric acid (296282-46-7)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 3.2: 75 percent / ethanol / 3 h / 65 °C 4.1: 54 percent / LiBH4 / tetrahydrofuran / 6 h / Heating 5.1: 66 percent / aq. HCl; AcOH / 7 h / Heating View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 3-isocyanato-3-[2-(4-octyl-phenyl)-ethyl]-dihydro-furan-2-one

Conditions	Yield
Multi-step reaction with 8 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: dimethylformamide / 3 h 4.1: 1 N aq. HCl / methanol / 5 h 5.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 6.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 7.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 8.1: benzene / 1 h / Heating View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 2-amino-2-[2-(4-octylphenyl)ethyl]butane-1,4-diol

Conditions

Yield

Multi-step reaction with 13 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: dimethylformamide / 3 h 4.1: 1 N aq. HCl / methanol / 5 h 5.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 6.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 7.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 8.1: benzene / 1 h / Heating 9.1: benzene / 7 h / Heating 10.1: LiBH4 / tetrahydrofuran / 0.5 h / Heating 11.1: pyridine / 13 h / 20 °C 12.1: Me3SiI / CH2Cl2 / 7 h 12.2: pyridine / 13 h 13.1: 2 M aq. LiOH / tetrahydrofuran; methanol / 2 h / Heating View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → N-[1-cyano-1-hydroxymethyl-3-(4-octylphenyl)propyl]acetamide (296282-78-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 3.2: 75 percent / ethanol / 3 h / 65 °C 4.1: 54 percent / LiBH4 / tetrahydrofuran / 6 h / Heating View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 3-[2-(4-octyl-phenyl)-ethyl]-2-oxo-tetrahydro-furan-3-carboxylic acid (1027589-49-6)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: dimethylformamide / 3 h 4.1: 1 N aq. HCl / methanol / 5 h 5.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 2-amino-2-[2-(4-octylphenyl)ethyl]pentane-1,5-diol

Conditions

Yield

Multi-step reaction with 11 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: 76 percent / dimethylformamide / 3 h 4.1: KOH / ethanol / 6 h / 50 °C 5.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 6.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 7.1: benzene / 1 h / Heating 8.1: benzene / 7 h / Heating 9.1: LiBH4 / tetrahydrofuran / 3 h / Heating 10.1: 5 N aq. KOH / tetrahydrofuran; methanol / 13 h / Heating 11.1: HCl; MeOH / diethyl ether / 0.5 h View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl) butan-2-yl) acetamide (249289-10-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 3.2: 61 percent / ethanol / 3 h / 65 °C 4.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 0.5 h 1.2: 3 h / 0 - 20 °C 2.1: sodium iodide / tetrahydrofuran / 20 °C 3.1: caesium carbonate / dimethyl sulfoxide / 3 h / 60 °C / Inert atmosphere 3.2: 60 - 80 °C 4.1: sodium tetrahydroborate / methanol / 20 °C View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 3-[2-(4-octyl-phenyl)-ethyl]-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester (1027929-75-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: dimethylformamide / 3 h 4.1: 1 N aq. HCl / methanol / 5 h View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 3-[2-(4-octyl-phenyl)-ethyl]-2-oxo-tetrahydro-furan-3-carbonyl azide

Conditions	Yield
Multi-step reaction with 7 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: dimethylformamide / 3 h 4.1: 1 N aq. HCl / methanol / 5 h 5.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 6.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 7.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → ethyl 2-acetamido-2-cyano-4-(4-octylphenyl)butyrate (296282-66-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 3.2: 75 percent / ethanol / 3 h / 65 °C View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 2-Methoxycarbonylamino-2-[2-(4-octylphenyl)ethyl]-γ-butyrolactone (177259-57-3)

Conditions

Yield

Multi-step reaction with 9 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: dimethylformamide / 3 h 4.1: 1 N aq. HCl / methanol / 5 h 5.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 6.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 7.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 8.1: benzene / 1 h / Heating 9.1: benzene / 7 h / Heating View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 2-Methoxycarbonylamino-2-[2-(4-octylphenyl)ethyl]butane 1,4-diol (177258-50-3)

Conditions

Yield

Multi-step reaction with 10 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: dimethylformamide / 3 h 4.1: 1 N aq. HCl / methanol / 5 h 5.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 6.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 7.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 8.1: benzene / 1 h / Heating 9.1: benzene / 7 h / Heating 10.1: LiBH4 / tetrahydrofuran / 0.5 h / Heating View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate (162358-09-0)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 3.2: 61 percent / ethanol / 3 h / 65 °C 4.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 5.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium iodide / butanone / 0.67 h / 0.8 - 0.85 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0.45 - 0.5 °C / Inert atmosphere 2.2: 0.4 - 0.45 °C / Inert atmosphere 3.1: calcium chloride / water; isopropyl alcohol / 0 h / 0.2 - 0.3 °C 3.2: 0.01 h / 0 - 0.5 °C 3.3: 0 h / 0.15 - 0.5 °C View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → C24H34O6

Conditions	Yield
Multi-step reaction with 6 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: dimethylformamide / 3 h 4.1: 1 N aq. HCl / methanol / 5 h 5.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 6.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 3-Acetamido-3-acetoxymethyl-5-(4-octylphenyl)pentyl acetate (177259-09-5)

Conditions

Yield

Multi-step reaction with 12 steps 1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: NaH / dimethylformamide / 0.5 h 3.2: dimethylformamide / 3 h 4.1: 1 N aq. HCl / methanol / 5 h 5.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 6.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 7.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 8.1: benzene / 1 h / Heating 9.1: benzene / 7 h / Heating 10.1: LiBH4 / tetrahydrofuran / 0.5 h / Heating 11.1: pyridine / 13 h / 20 °C 12.1: Me3SiI / CH2Cl2 / 7 h 12.2: pyridine / 13 h View Scheme

Upstream product

• 162358-04-5 acetic acid 2-(4-octylphenyl)ethyl ester 
• 17049-49-9 octylmagnesium bromide 
• 712223-57-9 acetic acid 2-[4-(trifluoromethanesulfonyloxy)phenyl]ethyl ester 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 58556-55-1 2-(4-hydroxyphenyl)ethyl acetate 
• 111-64-8 n-octanoic acid chloride 
• 103-45-7 acetic acid phenethyl ester 
• 162358-03-4 2-(4-octanoylphenyl)ethyl acetate 
• 219307-07-0 4'-(2-hydroxyethyl)octanophenone 
• 7440-44-0 pyrographite 
• 122-79-2 Phenyl acetate 
• 52914-23-5 4-iodophenethyl alcohol 
• 629-05-0 n-octyne 
• 111-85-3 n-chlorooctane 

Downstream Products

• 162358-06-7 4-octylphenethyl methanesulfonate 
• 162358-08-9 diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate 
• 162358-07-8 2-(4-octylphenyl)-1-iodoethane 
• 162359-55-9 fingolimod 
• 296282-46-7 2-amino-2-hydroxymethyl-4-(4-octyl-phenyl)-butyric acid 
• 296282-78-5 N-[1-cyano-1-hydroxymethyl-3-(4-octylphenyl)propyl]acetamide 
• 1027589-49-6 3-[2-(4-octyl-phenyl)-ethyl]-2-oxo-tetrahydro-furan-3-carboxylic acid 
• 249289-10-9 N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl) butan-2-yl) acetamide 
• 1027929-75-4 3-[2-(4-octyl-phenyl)-ethyl]-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 296282-66-1 ethyl 2-acetamido-2-cyano-4-(4-octylphenyl)butyrate 
• 177259-57-3 2-Methoxycarbonylamino-2-[2-(4-octylphenyl)ethyl]-γ-butyrolactone 
• 177258-50-3 2-Methoxycarbonylamino-2-[2-(4-octylphenyl)ethyl]butane 1,4-diol 
• 162358-09-0 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate 
• 177259-09-5 3-Acetamido-3-acetoxymethyl-5-(4-octylphenyl)pentyl acetate 

Relevant articles and documents

Development of novel PP2A activators for use in the treatment of acute myeloid leukaemia

AAL(S), the chiral deoxy analog of the FDA approved drug FTY720, has been shown to inhibit proliferation and apoptosis in several cancer cell lines. It has been suggested that it does this by activating protein phosphatase 2A (PP2A). Here we report the synthesis of new cytotoxic analogs of AAL(S) and the evaluation of their cytotoxicity in two myeloid cell lines, one of which is sensitive to PP2A activation. We show that these analogs activate PP2A in these cells supporting the suggested mechanism for their cytotoxic properties. Our findings identify key structural motifs required for anti-cancer effects.

PROCESS FOR PREPARATION OF FINGOLIMOD

The present invention provides a process for preparation of fingolimod, a compound of Formula I or a pharmaceutically acceptable salt thereof, free of regioisomeric impurity compound of Formula IA

PREPARATION OF FINGOLIMOD AND ITS SALTS

The present application provide processes for the preparation of fingolimod and its pharmaceutically acceptable salts, process for the purification of fingolimod hydrochloride and process for the preparation of amorphous fingolimod hydrochloride.