Benzyl Alcohol → Benzyl (2R)-hydroxy(phenyl)acetate

HRID 1682251Notes

Reaction equation

HRID 1682251 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].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 11914(-)-Mandelic acid

Product 1

HCID 853755Benzyl (2R)-hydroxy(phenyl)acetateYield 91.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 85.1 g (559 mmol) of D-mandelic acid, 65 ml (628 mmol) of benzyl alcohol, 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-bfe1c451b69e4199ba8a22d314b785bb
Source dataset
uspto-grants-1992_12
Patent number
US05175341

Reaction notes

Loading…