Formic Acid → Methyl 4-acetyl-3-hydroxybenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 3-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate (540 mg, 2.17 mmole) is combined with 4 ml formic acid under nitrogen. The reaction is warmed to 80° C. for 12 h, is cooled to rt, and the volatiles are removed in vacuo. The black residue is chromatographed over 25 g silica gel (230-400 mesh) eluting with 15% EtOAc/hexane. The appropriate fractions are combined and concentrated to provide 350 mg (83%) of methyl 4-acetyl-3-hydroxybenzoate as a pale yellow solid. 1H NMR (CDCl3) δ 2.70, 3.95, 7.54, 7.64, 7.82, 12.10 ppm.

Provenance & Evidence