Hydrogen Peroxide → (2R)-2-(4-methoxyphenyl)propanoic acid

Participants

Reaction Steps

A solution of (S)-3-((R)-2-(4-methoxyphenyl)propanoyl)-4-benzyloxazolidin-2-one (1.50 g, 4.42 mmol) in THF (20 ml) was added to a mixture of lithium hydroxide (750 mg, 17.6 mmol) and hydrogen peroxide (0.9 ml, 26.5 mmol, 30% in water). The reaction mixture was stirred at room temperature for 3 h. Then the solvent was evaporated, the residue was acidified with diluted HCl (10 ml) and extracted with DCM (3×50 ml). The combined organic layers was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude compound was purified by column chromatography over silica gel (60-120 mesh) using ethyl acetate (20%) in petroleum ether as eluent to afford 600 mg (76%) of (R)-2-(4-methoxyphenyl)propanoic acid as colorless liquid.

Provenance & Evidence