Acetic Anhydride → 4-Acetoxy-3-methylbenzoic acid

Participants

Reaction Steps

A solution of 5.42 g (35.6 mmol) of the 4-hydroxy-3-methylbenzoic acid in 50 ml of pyridine was added to 16.8 ml (178 mmol) of acetic anhydride. The resulting mixture was stirred overnight at room temperature, and the reaction mixture was distilled off under reduced pressure. The residue was dissolved in ethyl acetate. The resulting solution was washed with 2N hydrochloric acid and a saturated aqueous solution of sodium chloride and was then dried over Na2SO4. The solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate-hexane, whereby 3.64 g of 4-acetoxy-3-methylbenzoic acid were obtained as white powder (yield: 52.6%).

Provenance & Evidence