(S)-benzyl 2-hydroxy-2-phenylacetate

Base Information

• Chemical Name: (S)-benzyl 2-hydroxy-2-phenylacetate
• CAS No.: 62173-99-3
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• Hs Code.: 29181990
• DSSTox Substance ID: DTXSID601044499
• Nikkaji Number: J254.833J
• Mol file: 62173-99-3.mol

Synonyms:62173-99-3;L-(+)-Mandelic Acid Benzyl Ester;(S)-benzyl 2-hydroxy-2-phenylacetate;Benzyl (S)-(+)-mandelate;benzyl (2S)-2-hydroxy-2-phenylacetate;Benzyl L-(+)-Mandelate;benzyl L-mandelate;(S)-benzyl mandelate;Oprea1_804492;SCHEMBL5117818;(S)-mandelic acid, benzyl ester;JFKWZVQEMSKSBU-AWEZNQCLSA-N;DTXSID601044499;Benzyl (2S)-hydroxy(phenyl)acetate;Benzyl (S)-(+)-mandelate, 99%;MFCD00274325;AKOS015889531;CCG-242601;AS-62666;M1355;D91489;A868539;Benzeneaceticacid,a-hydroxy-,phenylmethyl ester,(as)-;Benzeneaceticacid, a-hydroxy-, phenylmethyl ester, (aS)-

Chemical Property of (S)-benzyl 2-hydroxy-2-phenylacetate

Chemical Property:

• Appearance/Colour: White or pale white crystalline powder
• Vapor Pressure: 1.13E-06mmHg at 25°C
• Melting Point: 107 ºC
• Refractive Index: 34 ° (C=1, CH3CN)
• Boiling Point: 386.8 ºC at 760 mmHg
• PKA: 12.15±0.20(Predicted)
• Flash Point: 163 °C
• PSA: 46.53000
• Density: 1.204 g/cm³
• LogP: 2.46340
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 253

Purity/Quality:

98%,99%, ^*data from raw suppliers

L-(+)-MandelicAcidBenzylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(C2=CC=CC=C2)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@H](C2=CC=CC=C2)O
• Uses: Benzyl (S)-(+)-mandelate can be used as a reactant to prepare: α-Hydroxy-N-(2-phenylethyl)benzenepropanamide by reacting with benzeneethanamine. Benzyl-2-fluoro-2-phenylacetate by deoxyfluorination of alcohols.

Technology Process of (S)-benzyl 2-hydroxy-2-phenylacetate

There total 32 articles about (S)-benzyl 2-hydroxy-2-phenylacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

benzyl oxo(phenyl)acetate (62977-82-6) → benzyl 2-hydroxy-2-phenylacetate (62173-99-3,80409-16-1,97415-09-3,890-98-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.25h;

DOI:10.1002/adsc.201100062

Reference yield: 94.0%

MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-hydroxy-2-phenylacetate (62173-99-3,80409-16-1,97415-09-3,890-98-2)

Guidance literature:

With salicylaldehyde; In toluene; at 25 - 70 ℃; for 14h; Solvent; Time; chemoselective reaction; Inert atmosphere;

DOI:10.1039/c2ra23068b

Reference yield: 92.0%

benzyl bromide (100-39-0) + MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2) → benzyl 2-hydroxy-2-phenylacetate (62173-99-3,80409-16-1,97415-09-3,890-98-2)

Guidance literature:

MANDELIC ACID; With caesium carbonate; In methanol; water; at 20 ℃; for 0.333333h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1002/adsc.201100062

upstream raw materials:

phenyldiazomethane

MANDELIC ACID

benzyl alcohol

2-Hydroxy-2-phenyl-1,1,1-tris-(phenylmercapto)-aethan

Downstream raw materials:

benzyl O-(tert-butyl)mandelate

bis((S)-2-(benzyloxy)-2-oxo-1-phenylethyl)phthalate

benzyl oxo(phenyl)acetate

(R)-benzyl 2-hydroxy-2-phenyl-acetate

Refernces

• 1、 Xu, Changming,Li, Xiangfan,Bai, Lei. "Direct Aerobic α-Hydroxylation of Arylacetates for the Synthesis of Mandelates". . p. 4298 - 4304. Retrieved 2022/03/16.
• 2、 Mahajani, Nivedita S.,Meador, Rowan I. L.,Smith, Tomas J.,Canarelli, Sarah E.,Adhikari, Arijit A.,Shah, Jigisha P.,Russo, Christopher M.,Wallach, Daniel R.,Howard, Kyle T.,Millimaci, Alexandra M.,Chisholm, John D.. "Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles". . p. 7871 - 7882. Retrieved 2019/06/27.