883723-47-5

Basic information

• Product Name: 2-ACETOXY-4-PHENYLBUTANOIC ACID
• Synonyms: 2-ACETOXY-4-PHENYLBUTANOIC ACID
• CAS NO: 883723-47-5
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 0
• Mol File: 883723-47-5.mol

Chemical Properties

• Boiling Point: 377.7°C at 760 mmHg
• Flash Point: 144.7°C
• Appearance: /
• Density: 1.189g/cm³
• Vapor Pressure: 2.23E-06mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: 2-ACETOXY-4-PHENYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETOXY-4-PHENYLBUTANOIC ACID(883723-47-5)
• EPA Substance Registry System: 2-ACETOXY-4-PHENYLBUTANOIC ACID(883723-47-5)

Safety Data

• Hazardous Substances Data: 883723-47-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H14O4/c1-9(13)16-11(12(14)15)8-7-10-5-3-2-4-6-10/h2-6,11H,7-8H2,1H3,(H,14,15)

Upstream product

• 235765-45-4 (S)-(-)-3-acetoxy-5-phenyl-2(5H)-furanone 
• 4263-93-8 2-hydroxy-4-phenylbutanoic acid 
• 108-24-7 acetic anhydride 
• 104-53-0 3-phenyl-propionaldehyde 
• 124-38-9 carbon dioxide 
• 1504663-35-7 1-dimethylphenylsilyl-3-phenylpropyl acetate 
• 1301234-48-9 C₁₆H₂₃NO₃ 
• 204511-99-9 (S)-3-[(E)-(S)-2-(1-Ethyl-1-methoxy-propyl)-pyrrolidin-1-ylimino]-5-phenyl-dihydro-furan-2-one 
• 148432-25-1 (S,S)-(+)-1-[3-Hydroxy-1-(2,6-di-tert-butyl-4-methoxy-1-phenoxycarbonyl)-3-phenyl-1-propylideneamino]-2-(1-ethyl-1-methoxypropyl)pyrrolidine 

Downstream Products

• 115016-95-0 (S)-2-hydroxy-4-phenylbutanoic acid 
• 117017-04-6 (R)-2-acetoxy-4-phenylbutanoic acid 
• 1173990-22-1 methyl 2-acetoxy-4-phenylbutanoate 
• 123736-87-8 (S)-2-acetoxy-4-phenylbutanoic acid 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 868532-38-1 acetic acid 3-phenyl-1-(2-thioxo-oxazolidine-3-carbonyl)-propyl ester 

Relevant articles and documents

Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives

In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.

A practical and inexpensive 'convertible' isonitrile for use in multicomponent reactions

N-tert-Butylamides are readily converted into the corresponding carboxylic acids by simple nitrosation. The process, which occurs under mild nonaqueous conditions, leaves carboxylic esters untouched and transforms multicomponent reaction products into useful building blocks for further synthetic elaboration.

Enantio-complementary deracemization of (±)-2-hydroxy-4- phenylbutanoic acid and (±)-3-phenyllactic acid using lipase-catalyzed kinetic resolution combined with biocatalytic racemization

Deracemization of (±)-3-phenyllactic acid (1) and (±)-2-hydroxy-4-phenylbutanoic acid (2) was accomplished by lipase-catalysed kinetic resolution coupled to biocatalytic racemization of the non-reacting substrate enantiomers using Lactobacillus paracasei DSM 20008. Cyclic repetition of this sequence led to a single enantiomeric product from the racemate. Access to both enantiomers was achieved by switching between lipase-catalysed acyl-transfer and ester hydrolysis reactions. Both products constitute important building blocks for virus protease- and ACE-inhibitors, respectively.

Kinetic resolution of α-acetoxy N-acyl oxazolidinethiones by a chiral O-nucleophilic acyl transfer catalyst

The kinetic resolution of α-acetoxy N-acyl oxazolidinethiones using the chiral, nonracemic O-nucleophilic acyl transfer catalyst 8 is described. The reaction proceeds on a variety of substrates in excellent yields, with s-factors ranging from 17 to 31. Copyright

Diastereo- and enantioselective synthesis of 4- and 3,4-substituted 2- acetoxy-butyrolactones

An efficient asymmetric synthesis of 4-mono-and 3,4-disubstituted 2- acetoxy-butyrolactones 2 has been developed, based on a hydrazone-mediated asymmetric aldol reaction, an intramolecular lactonization and a stereoselective hydrogenation of the resulting butenolides 1. An application of this process in the synthesis of the natural hunger substance 3 (ee = 90%) is also presented.