24817-51-4

Basic information

• Product Name: FEMA 3632
• Synonyms: FEMA 3632;2-PHENYLETHYL 2-METHYLBUTYRATE;ANATOLYL;2-methyl-butanoicaci2-phenylethylester;2-methyl-butyricaciphenethylester;benzylcarbinyl2-methylbutyrate;beta-phenylethylalpha-methylbutanoate;Butanoicacid,2-methyl-,2-phenylethylester
• CAS NO: 24817-51-4
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28
• EINECS: 246-476-5
• Mol File: 24817-51-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 305.14°C (rough estimate)
• Flash Point: >230 °F
• Appearance: Colourless liquid; sweet floral fruity odour with a warm, oily-herbaceous undertone
• Density: 0.975 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00347mmHg at 25°C
• Refractive Index: n20/D 1.486(lit.)
• CAS DataBase Reference: FEMA 3632(CAS DataBase Reference)
• NIST Chemistry Reference: FEMA 3632(24817-51-4)
• EPA Substance Registry System: FEMA 3632(24817-51-4)

Safety Data

• WGK Germany: 2
• RTECS: EK7902510
• Hazardous Substances Data: 24817-51-4(Hazardous Substances Data)

Usage

Chemical Properties

Phenethyl-2-methylbutyrate has a sweet, floral, fruity odor with warm, herbaceous notes; the flavor is sweet and slightly fruity

Occurrence

Reported found in mint.

Preparation

By esterification of phenethyl alcohol with α-methylbutyric acid.

Taste threshold values

Taste characteristics at 30 ppm: fruity, floral, green sweet and waxy.

Safety Profile

Low toxicity by ingestion and skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.

InChI:InChI=1/C13H18O2/c1-3-11(2)13(14)15-10-9-12-7-5-4-6-8-12/h4-8,11H,3,9-10H2,1-2H3

Synthetic route

2-oxo-3(RS)-methylvaleric acid (1460-34-0) + 2-phenylethanol (60-12-8) → 2-methyl-butanoic acid 2-phenylethyl ester (24817-51-4)

Conditions	Yield
With 3-nitro(diacetoxyiodo)benzene In dichloromethane at 20℃; for 24h; Sealed tube; Darkness; chemoselective reaction;	85%

1-butylene (106-98-9) + carbon monoxide (201230-82-2) + 2-phenylethanol (60-12-8) → 2-methyl-butanoic acid 2-phenylethyl ester (24817-51-4) + phenethylpentanoate (7460-74-4)

Conditions	Yield
With toluene-4-sulfonic acid; palladium(II) bromide; 2-(dicyclohexylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole In toluene at 100℃; under 30003 Torr; for 20h; Overall yield = 96 %; regioselective reaction;

butene-2 (107-01-7) + carbon monoxide (201230-82-2) + 2-phenylethanol (60-12-8) → 2-methyl-butanoic acid 2-phenylethyl ester (24817-51-4) + phenethylpentanoate (7460-74-4)

Conditions	Yield
With toluene-4-sulfonic acid; palladium(II) bromide; 2-(dicyclohexylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole In toluene at 100℃; under 30003 Torr; for 20h; Overall yield = 90 %; regioselective reaction;

Upstream product

• 106-98-9 1-butylene 
• 201230-82-2 carbon monoxide 
• 60-12-8 2-phenylethanol 
• 107-01-7 butene-2 
• 1460-34-0 2-oxo-3(RS)-methylvaleric acid 

Relevant articles and documents

Oxidative Decarboxylation Enables Chemoselective, Racemization-Free Esterification: Coupling of α-Ketoacids and Alcohols Mediated by Hypervalent Iodine(III)

An α-ketoacid could be converted into a reactive acylating agent by treatment with hypervalent iodine(III) species, and in so doing, we discovered a novel decarboxylative acylation of alcohols that affords a variety of esters in excellent yields. The esterification has been applied to a sterol bearing a free carboxylic acid and shows unique chemoselectivity. The procedure is racemization-free and operates under mild conditions.