Acetyl chloride → Methyl 2-methylbenzo[d]oxazole-6-carboxylate

Participants

Reaction Steps

To a solution of 4-amino-3-hydroxy-benzoic acid methyl ester (2085 mg, 12.47 mmmol) in xylene (200 mL) were added acetyl chloride (1.06 mL, 14.96 mmol), pyridinium p-toluenesulfonate (940 mg, 3.74 mmol) and triethylamine (2.09 mL, 14.96 mmol), and the solution was stirred for 8.5 hours under reflux. Ethyl acetate was added to the reaction mixture, which was then washed with water, dried over anhydrous magnesium sulfate, then, evaporated in vacuo, the resulting residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (1917 mg, 10.02 mmol, 80.4%) was obtained.

Provenance & Evidence