Acetone → p-Methoxyphenylpropionic acid

HRID 1164759Notes

Reaction equation

HRID 1164759 reaction equation
Cl[CH:2](C)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[CH2:14]1[O:17]C1C.CC(C)=[O:20]>[Hg]>[CH3:12][O:11][C:8]1[CH:7]=[CH:6][C:5]([CH:3]([CH3:2])[C:14]([OH:17])=[O:20])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6378Propylene OxideHCID 37278952-chloro-1-(4-methoxyphenyl)propan-1-one

Product 1

HCID 257576p-Methoxyphenylpropionic acid

Reagents, catalysts & solvents 1

HCID 23931MercuryCatalyst

Procedure

A solution comprising 15 parts of 2-chloro-1-(4'-methoxyphenyl)-1-propanone and 10 parts of propylene oxide in 500 parts of 10% v/v aqueous acetone was irradiated by means of a 450W mercury vapour lamp for 8 hours. The solvent was removed by distillation and the resulting acid was extracted with 5% w/v aqueous sodium hydroxide. Acidification yielded 9.5 parts of α-(4'-methoxyphenyl)-propionic acid, m.p. 55° C. to 57° C.

Workup

  1. customThe solvent was removed by distillation
  2. extractionthe resulting acid was extracted with 5% w/v aqueous sodium hydroxide

Sources & evidence

ORD record
ord-2bc4c132720d4f8c88e02dad5df98d21
Source dataset
uspto-grants-1990_03
Patent number
US04906343

Reaction notes

Loading…