(R)-(-)-alpha-methoxyphenylacetic acid → (R)-Cyclohexyl-methoxy-acetic acid

HRID 252383Notes

Reaction equation

HRID 252383 reaction equation
[CH3:1][O:2][C@H:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5]>CO>[CH:7]1([C@@H:3]([O:2][CH3:1])[C:4]([OH:6])=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 1

HCID 2724294(R)-(-)-alpha-methoxyphenylacetic acid

Product 1

HCID 66888902(R)-Cyclohexyl-methoxy-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An autoclave is charged with a solution of 1.00 g of (R)-α-methoxy-phenyl acetic acid [24190-08-7] in 20 ml methanol. 0.100 g of Nishimura catalyst are added and the mixture is hydrogenated at 4 bar and 20° C. for 1 hour. The mixture is filtered over Hyflo and the filtrate concentrated by evaporation to provide the title compound as a colourless oil. The crude material is used without further purification. Rf=0.84 (150:54:10:1 dichloromethane-methanol-water-acetic acid).

Workup

  1. filtrationThe mixture is filtered over Hyflo
  2. concentrationthe filtrate concentrated by evaporation

Sources & evidence

ORD record
ord-c53d2b17f8754b31ad33100a70706f62
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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