Methanol → 3-Methyl-2-phenylbutanoic acid

HRID 1655763Notes

Reaction equation

HRID 1655763 reaction equation
C[O:2][C:3](=[O:14])[CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:5]([CH3:7])[CH3:6].[OH-].[Na+].CO>O>[C:8]1([CH:4]([CH:5]([CH3:7])[CH3:6])[C:3]([OH:14])=[O:2])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 5051294Methyl 3-methyl-2-phenylbutanoate

Product 1

HCID 190243-Methyl-2-phenylbutanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 165.8 g (0.87 mol) of 2-phenyl-3-methylbutyric acid methyl ester, 52.0 q (1.30 mol) of sodium hydroxide, 1200 ml of methanol and 600 ml of water was heated to reflux for one hour. After evaporation of the methanol under reduced pressure, dilution with water and acidification with conc. hydrochloric acid, the aqueous solution was extracted with ether. The ethereal extracts were washed with water, dried over sodium sulfate and evaporated under reduced pressure, to obtain 146.3 g (95%) of 2-phenyl-3-methylbutyric acid in the form of a yellow oil which was used directly in the next step.

Workup

  1. temperatureto reflux for one hour
  2. customAfter evaporation of the methanol under reduced pressure, dilution with water and acidification with conc. hydrochloric acid
  3. extractionthe aqueous solution was extracted with ether
  4. washThe ethereal extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-57c4711cb01c4faab9579c4ee218d0fb
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

Loading…