3-Hydroxybenzoic Acid → Benzyl 3-hydroxybenzoate

Participants

Reaction Steps

4.14 g (30 mmol) of 3-hydroxybenzoic acid was dissolved in 250 ml of N,N-dimethylformamide, and 2.49 g (18 mmol) of potassium carbonate and 3.8 ml (33 mmol) of benzyl chloride were added, followed by stirring at room temperature overnight. After the reaction solution was concentrated under vacuum, the residue was dissolved in ethyl acetate and 5% aqueous solution of sodium hydrogencarbonate. The organic layer was washed with 5% aqueous solution of sodium hydrogencarbonate, distilled water, and then with saturated brine, dried over anhydrous magnesium sulfate. This solution was concentrated under vacuum and the residue was crystallized from ethyl acetate-hexane to obtain 3.96 g of benzyl 3-hydroxybenzoate (yield 58%).

Provenance & Evidence