Hydrochloric Acid → Benzyl 4-benzyloxy-2-chlorobenzoate

Participants

Reaction Steps

To a solution of 2-chloro-4-hydroxybenzoic acid (695 mg) in N,N-dimethylformamide (3.5 ml) were added potassium carbonate (1.67 g) and benzyl bromide (1.73 g) and the mixture was stirred at room temperature for 14 hr. To the reaction mixture was added 1N hydrochloric acid and the resulting product was extracted 3 times with diethyl ether. The organic layers were combined and washed successively with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was recrystallized from diisopropyl ether/hexane to give benzyl 4-benzyloxy-2-chlorobenzoate (1.13 g) as a pale-yellow powder.

Provenance & Evidence