Acetic Anhydride → 3,5-Dimethyl-4-acetoxybenzoic acid

Participants

Reaction Steps

To a solution of 4-hydroxy-3,5-dimethyl-benzoic acid (1) (5.41 g, 32.5 mmol) in anhydrous pyridine (50 mL) were added acetic anhydride and 4-dimethylaminopyridine (0.1 g, 0.8 mmol). The reaction mixture was stirred at room temperature for 16 hours. Pyridine was evaporated under reduced pressure. The residue was taken in ethyl acetate (300 mL). The organic phase was washed with 2 N aq. HCl (100 mL), water (2×100 mL), brine (100 mL) and dried over anhydrous Na2SO4. Solvent was evaporated to give 4-acetoxy-3,5-dimethylbenzoic acid (2) as an off-white solid. Yield: 6.65 g (98%).

Provenance & Evidence