Water → tert-Butyl (4-formylphenyl)carbamate

Participants

Reaction Steps

Chromium trioxide (2.4 g) is added in portions to pyridine (29 mL) to maintain the temperature between 0°–10° C. A yellow suspension is formed. A solution of (4-hydroxymethylphenyl)carbamic acid tert-butyl ester (1.8 g) in pyridine (29 mL) is added dropwise to the yellow suspension. The reaction mixture is warmed to room temperature and stirred for 30 minutes. The reaction mixture is poured into water and extracted twice with ethyl acetate. The combined organics are washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated under reduced pressure and chromatographed on silica gel (4:1 ethyl acetate/hexane used as eluant) to give 1.09 g product as a white solid. MS: m/z 222 (M+H)+.

Provenance & Evidence