Water → Benzyl 2,4-dihydroxybenzoate

Participants

Reaction Steps

15.4 g (0.1 mol) of 2,4-dihydroxybenzoic acid dissolved in 50 ml of DMF are added dropwise to a solution of 3 g (0.1 mol) of sodium hydride (80% in oil) and 50 ml of DMF and the mixture is stirred at room temperature until evolution of gas has ceased. 13.1 ml (0.1 mol) of benzyl bromide are then added and the mixture is stirred at room temperature until the reaction mixture has dissolved. The reaction mixture is poured into water and extracted with ethyl ether, and the organic phase is separated, washed with water, dried over magnesium sulphate and evaporated. The residue is purified by chromatography on a silica column, eluting with dichloromethane. 19.7 g (81%) of the expected ester are collected, which melts at 94°-95° C.

Provenance & Evidence