(+-)-3-Phenyllactic acid → 2-Acetoxy-3-phenylpropanoic acid

HRID 1379109Notes

Reaction equation

HRID 1379109 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8]>>[C:1]([O:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 3848(+-)-3-Phenyllactic acidHCID 6367Acetyl chloride

Product 1

HCID 111065762-Acetoxy-3-phenylpropanoic acidYield 100.4%

Procedure

4.83 g (61.53 mmol) of acetyl chloride are added to 8.88 g (53.49 mmol) of (RS)-2-hydroxy-3-phenyl propanoic acid. The mixture is refluxed for 30 minutes. The excess acetyl chloride is evaporated. 11.18 g of (RS)-2-acetyloxy-3-phenyl propanoic acid are obtained.

Workup

  1. temperatureThe mixture is refluxed for 30 minutes
  2. customThe excess acetyl chloride is evaporated

Sources & evidence

ORD record
ord-eee642f525ed4ad9b53c872742832daf
Source dataset
uspto-grants-1997_09
Patent number
US05670531

Reaction notes

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