56196-53-3

Basic information

• Product Name: ETHYL 4-METHYLOCTANOATE
• Synonyms: ETHYL 4-METHYLOCTANOATE;EINECS 260-051-1;4-Methyloctanoic acid ethyl ester;Oryctalure;Ethyl 4-metiloctanoate
• CAS NO: 56196-53-3
• Molecular Formula: C₁₁H₂₂O₂
• Molecular Weight: 186.29
• EINECS: 260-051-1
• Mol File: 56196-53-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 214.2°Cat760mmHg
• Flash Point: 82.9°C
• Appearance: /
• Density: 0.87g/cm³
• Vapor Pressure: 0.158mmHg at 25°C
• Refractive Index: 1.425
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: ETHYL 4-METHYLOCTANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-METHYLOCTANOATE(56196-53-3)
• EPA Substance Registry System: ETHYL 4-METHYLOCTANOATE(56196-53-3)

Safety Data

• Hazardous Substances Data: 56196-53-3(Hazardous Substances Data)

Usage

Uses

Oryctalure was used for identification of olfactory stimulants for Anopheles gambiae from human sweat samples.

InChI:InChI=1/C11H22O2/c1-4-6-7-10(3)8-9-11(12)13-5-2/h10H,4-9H2,1-3H3

Synthetic route

diethyl 2-methylhexylmalonate (63037-60-5) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
With water; sodium chloride In N,N-dimethyl acetamide at 139℃; for 13.5h; Krapcho Dealkoxycarbonylation;	96.9%
Multi-step reaction with 2 steps 1: aq.-ethanolic KOH-solution / und Erhitzen des nach dem Ansaeuern erhaltenen Reaktionsprodukts im Vakuum bis auf 170grad 2: toluene; sulfuric acid View Scheme

2-iodohexane (18589-27-0) + ethyl acrylate (140-88-5) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
With borohydride exchange resin; nickel diacetate In methanol at 20℃; for 1h;	92%
With borohydride exchange resin; nickel diacetate In methanol for 1h; Ambient temperature;	92%

1-chloro-2-methylhexane + diethyl malonate (105-53-3) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
Stage #1: 1-chloro-2-methylhexane; diethyl malonate With potassium carbonate; sodium iodide In N,N-dimethyl acetamide at 130℃; for 9h; Stage #2: With water In N,N-dimethyl acetamide at 116℃; for 12h;	79.8%

1-chloro-2-methylhexane + diethyl malonate (105-53-3) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3) + diethyl 2-methylhexylmalonate (63037-60-5)

Conditions	Yield
With caesium carbonate; potassium iodide In N,N-dimethyl acetamide at 130℃; for 8h;	A 41.66% B 42.3%

ethyl γ-iodovalerate (79909-21-0) + butyl magnesium bromide (693-04-9) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
With [((Me)NN2)NiCl] In tetrahydrofuran; ISOPROPYLAMIDE at -35 - 20℃; Inert atmosphere;	35%

dihydro-5-butyl-5-methyl-2-(3H)-furanone (3285-00-5) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
With thionyl chloride; benzene Erhitzen einer mit Chlorwasserstoff gesaettigten Loesung des Reaktionsgemisches in Aethanol und Hydrieren des Reaktionsprodukts an Platin in Aethanol;

ethanol (64-17-5) + rac-4-methyloctanoic acid (54947-74-9) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
With sulfuric acid; toluene

ethyl 4-methyleneoctanoate (944721-57-7) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; for 3h;

2-methylenehexan-1-ol (50965-90-7) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / propionic acid / 5 h / 138 °C 2: H2 / Pd/C / ethanol / 3 h / 20 °C View Scheme

2-n-butylacrolein (1070-66-2) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaBH4; aq. NaHCO3 / methanol / 1 h / 5 °C 2: 76 percent / propionic acid / 5 h / 138 °C 3: H2 / Pd/C / ethanol / 3 h / 20 °C View Scheme

hexanal (66-25-1) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethylamine hydrochloride / H2O / 24 h / 70 °C 2: NaBH4; aq. NaHCO3 / methanol / 1 h / 5 °C 3: 76 percent / propionic acid / 5 h / 138 °C 4: H2 / Pd/C / ethanol / 3 h / 20 °C View Scheme

1-iodo-2-methyl-hexane (624-21-5) → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol 2: aq.-ethanolic KOH-solution / und Erhitzen des nach dem Ansaeuern erhaltenen Reaktionsprodukts im Vakuum bis auf 170grad 3: toluene; sulfuric acid View Scheme

1-chloro-2-methylhexane → (+/-)-Ethyl 4-methyloctanoate (56196-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl acetamide / 10 h / 130 °C 2: sodium chloride; water / N,N-dimethyl acetamide / 13.5 h / 139 °C View Scheme

(+/-)-Ethyl 4-methyloctanoate (56196-53-3) → rac-4-methyloctanoic acid (54947-74-9)

Conditions	Yield
With potassium hydroxide In ethanol for 2.5h; Heating;	95%

(+/-)-Ethyl 4-methyloctanoate (56196-53-3) → 4-methyloctan-1-ol (38514-03-3)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether Reduction; Heating;	75%
With lithium aluminium tetrahydride; diethyl ether

(+/-)-Ethyl 4-methyloctanoate (56196-53-3) → 1-Bromo-4-methyloctane (191925-28-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 100 percent / PPh3; Br2 / CH2Cl2 / 0.5 h View Scheme

(+/-)-Ethyl 4-methyloctanoate (56196-53-3) → 10,14-Dimethyloctadec-1-ene

Conditions

Yield

Multi-step reaction with 7 steps 1.1: 75 percent / LiAlH4 / diethyl ether / Heating 2.1: 100 percent / PPh3; Br2 / CH2Cl2 / 0.5 h 3.1: Mg / diethyl ether / 1 h / Heating 3.2: 60 percent / diethyl ether 4.1: Et3N / tetrahydrofuran / 1 h 5.1: trimethyltetradecylammonium bromide / tetrahydrofuran 5.2: HF; H2O / acetonitrile / 2 h 5.3: H2 / 5 percent Pd/C / hexane 6.1: 96 percent / PPh3; Br2 / CH2Cl2 / 0.5 h 7.1: 71 percent / LDA / tetrahydrofuran View Scheme

(+/-)-Ethyl 4-methyloctanoate (56196-53-3) → 10,14-Dimethyloctadecanol (191925-36-7)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 75 percent / LiAlH4 / diethyl ether / Heating 2.1: 100 percent / PPh3; Br2 / CH2Cl2 / 0.5 h 3.1: Mg / diethyl ether / 1 h / Heating 3.2: 60 percent / diethyl ether 4.1: Et3N / tetrahydrofuran / 1 h 5.1: trimethyltetradecylammonium bromide / tetrahydrofuran 5.2: HF; H2O / acetonitrile / 2 h 5.3: H2 / 5 percent Pd/C / hexane View Scheme

(+/-)-Ethyl 4-methyloctanoate (56196-53-3) → 1-Bromo-10,14-dimethyloctadecane (191925-39-0)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: 75 percent / LiAlH4 / diethyl ether / Heating 2.1: 100 percent / PPh3; Br2 / CH2Cl2 / 0.5 h 3.1: Mg / diethyl ether / 1 h / Heating 3.2: 60 percent / diethyl ether 4.1: Et3N / tetrahydrofuran / 1 h 5.1: trimethyltetradecylammonium bromide / tetrahydrofuran 5.2: HF; H2O / acetonitrile / 2 h 5.3: H2 / 5 percent Pd/C / hexane 6.1: 96 percent / PPh3; Br2 / CH2Cl2 / 0.5 h View Scheme

(+/-)-Ethyl 4-methyloctanoate (56196-53-3) → 1-tert-Butyldimethylsilyloxy-10,14-dimethyl-10-octadecanol (191925-33-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 75 percent / LiAlH4 / diethyl ether / Heating 2.1: 100 percent / PPh3; Br2 / CH2Cl2 / 0.5 h 3.1: Mg / diethyl ether / 1 h / Heating 3.2: 60 percent / diethyl ether View Scheme

(+/-)-Ethyl 4-methyloctanoate (56196-53-3) → methanesulfonic acid 10-(tert-butyl-dimethyl-silanyloxy)-1-methyl-1-(4-methyl-octyl)-decyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 75 percent / LiAlH4 / diethyl ether / Heating 2.1: 100 percent / PPh3; Br2 / CH2Cl2 / 0.5 h 3.1: Mg / diethyl ether / 1 h / Heating 3.2: 60 percent / diethyl ether 4.1: Et3N / tetrahydrofuran / 1 h View Scheme

Upstream product

• 3285-00-5 dihydro-5-butyl-5-methyl-2-(3H)-furanone 
• 64-17-5 ethanol 
• 54947-74-9 rac-4-methyloctanoic acid 
• 18589-27-0 2-iodohexane 
• 140-88-5 ethyl acrylate 
• 944721-57-7 ethyl 4-methyleneoctanoate 
• 50965-90-7 2-methylenehexan-1-ol 
• 1070-66-2 2-n-butylacrolein 
• 66-25-1 hexanal 
• 624-21-5 1-iodo-2-methyl-hexane 
• 63037-60-5 diethyl 2-methylhexylmalonate 
• 79909-21-0 ethyl γ-iodovalerate 
• 693-04-9 butyl magnesium bromide 
• 105-53-3 diethyl malonate 

Downstream Products

• 38514-03-3 4-methyloctan-1-ol 
• 54947-74-9 rac-4-methyloctanoic acid 

Relevant articles and documents

METHOD FOR PRODUCING ETHYL 4-METHYLOCTANOATE

There is provided a method for producing ethyl 4-methyloctanoate at a lower cost, by fewer steps, and in higher yield. More specifically, there is provided a method for producing ethyl 4-methyloctanoate comprising the steps of: reacting 1-chloro-2-methylhexane through malonic ester synthesis to obtain diethyl 2-methylhexylmalonate, and subjecting the diethyl 2-methylhexylmalonate to a Krapcho reaction to obtain ethyl 4-methyloctanoate.

Efficient synthesis of (±)-4-methyloctanoic acid, aggregation pheromone of rhinoceros beetles of the genus oryctes (Coleoptera: Dynastidae, Scarabaeidae)

(±)-4-Methyloctanoic acid and its ethyl ester are aggregation pheromones of many rhinoceros beetles of the genus Oryctes and are investigated for the control of these pests by olfactory trapping. A simple, economical, and high-yield (>50%) synthesis of (±)-4-methyloctanoic acid and its ethyl ester is presented starting from n-hexanal. The key step in this sequence is an orthoester Claisen rearrangement for the elongation of the carbon chain by two.

A new coupling reaction of alkyl iodides with α,β-unsaturated esters using Ni2B(cat.)-BER in methanol

Alkyl iodides can be coupled with α,β-unsaturated esters using Ni2B(0.05-0.2 eq)-BER(3 eq) in methanol at room temperature. Products (68-95%) are conveniently isolated, simply filtering the resin and evaporating the excess enoates and methanol.