p-Toluenesulfonic acid → Benzyl (2R)-hydroxy(phenyl)acetate

HRID 2255802Notes

Reaction equation

HRID 2255802 reaction equation
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15](S(O)(=O)=O)=[CH:14][CH:13]=1>C1C=CC=CC=1>[C:1]([O:11][CH2:22][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11914(-)-Mandelic acid

Product 1

HCID 853755Benzyl (2R)-hydroxy(phenyl)acetateYield 9,528.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 85.1 g (559 mmol) of D-mandelic acid, 65 ml(628 mmol) of benzyl alchohol, and 1.01 g (5.35 mmol) of p-toluenesulfonic acid in 700 ml of benzene was refluxed for 6.5 hours. The mixture was washed with water and concentrated. The residue was recrystallized from ether to give 123.5 g of the aimed compound D-2 in 91% yield.

Workup

  1. washThe mixture was washed with water
  2. concentrationconcentrated
  3. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-38531b64c1ed41c7836351758cbadbaf
Source dataset
uspto-grants-1993_08
Patent number
US05241104

Reaction notes

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