Benzyl Chloride → Benzyl 2-acetamido-4-(benzyloxy)benzoate

Participants

Reaction Conditions

Reaction Steps

A suspension of 1.1 g (5.64 mmol) of 2-acetylamino-4-hydroxy-benzoic acid (preparation: Recl. Trav. Chim. Pays-Bas, 72, p195, 1953), 1.6 ml (13.53 mmol) of benzyl chloride, 3.9 g (28.18 mmol) of potassium carbonate in DMF (15 ml) was stirred at 80° C. for 17 h under argon. The reaction mixture was concentrated in vacuo and partitioned between CH2Cl2 and water. The layers were separated, the aqueous layer once extracted with CH2Cl2, the organic layers combined, washed with brine, dried over MgSO4 and concentrated in vacuo, to give 1.89 g (85.75%) of the desired 2-acetylamino-4-benzyloxy-benzoic acid benzyl ester as an off-white solid. ISP mass spectrum, m/e: 376.5 (M+1 calculated for C23H21NO4: 375.42).

Provenance & Evidence