138276-21-8

Basic information

• Product Name: Benzenebutanoic acid, a-hydroxy-, phenylmethyl ester, (S)-
• CAS NO: 138276-21-8
• Molecular Formula: C17H18O3
• Molecular Weight: 270.328
• Mol File: 138276-21-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenebutanoic acid, a-hydroxy-, phenylmethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenebutanoic acid, a-hydroxy-, phenylmethyl ester, (S)-(138276-21-8)
• EPA Substance Registry System: Benzenebutanoic acid, a-hydroxy-, phenylmethyl ester, (S)-(138276-21-8)

Safety Data

• Hazardous Substances Data: 138276-21-8(Hazardous Substances Data)

Upstream product

• 1760-46-9 diphenylacetic anhydride 
• 109684-03-9 benzyl 2(R)-hydroxy-4-phenylbutyrate 
• 117-34-0 2,2-diphenylacetic acid 

Relevant articles and documents

METHOD FOR PRODUCING OPTICALLY ACTIVE 2-HYDROXY ESTER AND NOVEL INTERMEDIATE COMPOUND

Disclosed is a method for producing an optically active 2-hydroxy ester, comprising selectively esterifying one enantiomer of a racemic 2-hydroxy ester in a solvent containing a catalyst such as tetramisole or benzotetramisole, and a carboxylic acid anhydride, or a carboxylic acid anhydride and a carboxylic acid. In particular, in the case where the solvent contains a carboxylic acid anhydride, but does not contain a carboxylic acid, as the carboxylic acid anhydride, a carboxylic acid anhydride containing a tertiary or quaternary carbon atom in the a-position is used. On the other hand, in the case where the solvent contains a carboxylic acid anhydride and a carboxylic acid, as the carboxylic acid, a carboxylic acid containing a tertiary or quaternary carbon atom in the a-position is used.

Kinetic resolution of the racemic 2-hydroxyalkanoates using the enantioselective mixed-anhydride method with pivalic anhydride and a chiral acyl-transfer catalyst

A variety of optically active 2-hydroxyalkanoates and the corresponding 2-acyloxyalkanoates are produced by the kinetic resolution of racemic 2-hydroxyalkanoates by using achiral 2,2-diarylacetic acid with hindered carboxylic anhydrides as the coupling reagents. The combined use of diphenylacetic acid, pivalic anhydride, and (+)-(R)-benzotetramisole ((R)-BTM) effectively produces (S)-2-hydroxyalkanoates and (R)-2-acyloxyalkanoates from the racemic 2-hydroxyalkanoates (s-values = 47-202). This protocol directly provides the desired chiral 2-hydroxyalkanoate derivatives from achiral diarylacetic acid and racemic secondary alcohols that do not include the sec-phenethyl alcohol moiety by using the transacylation process to generate the mixed anhydrides from the acid components with bulky carboxylic anhydrides under the influence of the chiral acyl-transfer catalyst. The transition state that provides the desired (R)-2-acyloxyalkanoate from (R)-2-hydroxyalkanoate included in the racemic mixture is disclosed by DFT calculations, and the structural features of the transition form are also discussed.