Potassium Permanganate → 2-[(1,1-Dimethylethyl)oxy]-6-chlorobenzoic acid

Participants

Reaction Steps

To a solution of 2-[(1,1-dimethylethyl)oxy]-6-chlorobenzaldehyde (8.40 g, 40.0 mmol) in t-butanol (200 mL) was added 1.25M KH2PO4 (pH 7, 200 mL) and 0.4M aqueous potassium permanganate (200 mL, 80 mmol). The reaction was stirred at room temperature for 3 h and was quenched by the addition of saturated aqueous sodium sulfite (200 mL). The brown suspension was acidified with 2N HCl with ice-cooling until the MnO2 dissolved (pH 4). The reaction was extracted with ethyl acetate (3 times) and the organic layers were washed with brine, dried (MgSO4) and concentrated to a white solid. The crude product was recrystallized from hexanes at 0° C. to afford 7.14 g (78%) of 2-[(1,1-dimethylethyl)oxy]-6-chlorobenzoic acid as white crystals: mp 117°-119° C.

Provenance & Evidence