(R)-Benzyl 2-hydroxy-2-phenylacetate

Base Information

• Chemical Name: (R)-Benzyl 2-hydroxy-2-phenylacetate
• CAS No.: 97415-09-3
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• Hs Code.: 29181990
• European Community (EC) Number: 640-042-2
• DSSTox Substance ID: DTXSID50357490
• Nikkaji Number: J254.832A
• Wikidata: Q72488155
• Mol file: 97415-09-3.mol

Synonyms:97415-09-3;(R)-Benzyl 2-hydroxy-2-phenylacetate;Benzyl (R)-(-)-mandelate;(R)-benzyl Mandelate;D-(-)-Mandelic Acid Benzyl Ester;benzyl (2R)-2-hydroxy-2-phenylacetate;Benzyl D-mandelate;MFCD00674031;Benzyl D-(-)-Mandelate;(-)-Mandelic acid benzyl ester;D-Mandelic Acid Benzyl Ester;SCHEMBL2231648;DTXSID50357490;JFKWZVQEMSKSBU-CQSZACIVSA-N;HMS3650E03;Benzyl (2R)-hydroxy(phenyl)acetate;Benzyl (R)-(-)-mandelate, 99%;AKOS005256826;M1354;A24810;F16500;HYDROXY-PHENYL-ACETIC ACID BENZYL ESTER;SR-01000946772;SR-01000946772-1;Benzeneacetic acid,a-hydroxy-,phenylmethyl ester,(ar)-;R)-Benzyl mandelate;D-(-)-Mandelic acid benzyl ester;Benzyl d-(-)-mandelate;Benzyl (r)-(-)-mandelate;Benzyl D-(-)-mandelate

Chemical Property of (R)-Benzyl 2-hydroxy-2-phenylacetate

Chemical Property:

• Vapor Pressure: 1.13E-06mmHg at 25°C
• Melting Point: 104-107 °C(lit.)
• Refractive Index: -34 ° (C=1, CH3CN)
• Boiling Point: 386.8 °C at 760 mmHg
• PKA: 12.15±0.20(Predicted)
• Flash Point: 163 °C
• PSA: 46.53000
• Density: 1.204 g/cm³
• LogP: 2.46340
• Storage Temp.: Sealed in dry,Room Temperature
• 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% ^*data from raw suppliers

D-(-)-MandelicAcidBenzylEster ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

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
• Description: (R)-benzyl Mandelate is a synthetic intermediate useful for pharmaceutical synthesis.
• Uses: Benzyl (R)-(-)-mandelate can be employed as reactant to synthesize: (S)-α-Hydroxy-N-(2-phenylethyl)benzenepropanamide (α-hydroxyamides) by enzyme catalyzed amidation reaction. Optically pure (R)- monomethyl esters of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic acid, which is employed in the preparation of HMG-CoA reductase inhibitors. O-Ibuprofenylmandelic acid via acylation reaction with optically active ibuprofen and subsequent hydrogenation. Benzyl (R)-2-fluoro-2-phenylacetate via deoxyfluorination of alcohols using AlkylFluor.It can also be used to prepare HMG-CoA reductase inhibitors. D-(-)-Mandelic Acid Benzyl Ester is a useful reagent for the preparation of a pharmaceutical composition for treating atopic dermatitis.

Technology Process of (R)-Benzyl 2-hydroxy-2-phenylacetate

There total 34 articles about (R)-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: 98.0%

(R)-Mandelic Acid (611-71-2) + benzyl bromide (100-39-0) → (R)-benzyl 2-hydroxy-2-phenyl-acetate (97415-09-3)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1080/00397910008086893

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

upstream raw materials:

phenyldiazomethane

MANDELIC ACID

benzyl alcohol

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

Downstream raw materials:

benzyl oxo(phenyl)acetate

4-(benzyloxy)-5-phenylfuran-2(5H)-one

benzyl 2-phenylacetate

benzyl O-(tert-butyl)mandelate

Refernces

• 1、 Gao, Yang,Zhang, Xuexin,Laishram, Ronibala Devi,Chen, Jingchao,Li, Kangkui,Zhang, Keyang,Zeng, Guangzhi,Fan, Baomin. "Cobalt-Catalyzed Transfer Hydrogenation of α-Ketoesters and N-Cyclicsulfonylimides Using H2O as Hydrogen Source". supporting information. p. 3991 - 3997. Retrieved 2019/08/02.
• 2、 Gallo, Rafael Douglas C.,Burtoloso, Antonio C. B.. "Silica-supported HClO4 promotes catalytic solvent- and metal-free O-H insertion reactions with diazo compounds". . p. 4547 - 4556. Retrieved 2018/10/17.