4-Methoxybenzoic Acid → p-Anisoyl chloride

Participants

Reaction Steps

Thionyl chloride (10 mL) was added to 4-methoxybenzoic acid (306 mg, 2.0 mmol) and the mixture was stirred at reflux for 3 hr. Thionyl chloride was evaporated under reduced pressure and the residues was dried in vacuum to obtain 4-methoxybenzoyl chloride (320 mg). 3-Hydroxyanthranilic acid (167 mg, 1.0 mmol) and pyridine (158 mg, 2.0 mmol) were added to dichlormethane (10 mL) and the mixture was stirred at room temperature for 30 min. Then 2 (320 mg, 2.0 mmol) was added. The mixture was stirred at room temperature overnight and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1 to 10:1) to yield methyl 3-hydroxy-2-(4-methoxybenzamido)benzoate as a solid (178 mg, yield 59%). LC-MS (ESI) m/z 302 [M+1]+.

Provenance & Evidence