4-Hydroxybenzoic Acid → 4-(Benzyloxy)benzoic acid

Participants

Reaction Steps

A solution of 4-hydroxybenzoic acid (5.52 g; 0.40 mole), benzyl bromide (11.89 mL; 0.1 mol) and tricaprylylmethylammonium chloride (100 mg, Aliquat 336® Henkel Corporation) in methanol (50 mL) was refluxed in presence of potassium carbonate (16.52 g) for 12 hours. The reaction mixture was then poured slowly into a solution of 2N hydrochloric acid solution. The precipitated acid was filtered, dried and recrystallized from hexane/ethyl acetate to give 5 g of 4-benzyloxybenzoic acid (yield=55%).

Provenance & Evidence