Allyl bromide → 3-Chloromethyl-benzoic acid allyl ester

Participants

Reaction Steps

A solution of 3-(chloromethyl)-benzoic acid (50.0 g, 0.293 mol), potassium carbonate (48.61 g, 0.352 mol) and allyl bromide (50.7 mL, 0.586 mol) in acetone (500 mL) is refluxed for 2 hours, after which time the solution is cooled to room temperature and filtered through celite. The filtrate is evaporated and the residue chromatographed (silica, 5% EtOAc/hexane) to yield allyl 3-(chloromethyl)-benzoate as a clear oil.

Provenance & Evidence