Hydrochloric Acid → Methyl Benzoate

Participants

Reaction Steps

To a cooled (0° C.) solution of 27 mg (1.17 m atoms) of sodium in 4 ml of absolute methanol there were added 78 mg (0.47 mmol) of methyl thiosalicylate. After stirring 5 minutes, a solution of 128 mg (0.39 mmol) of the foregoing mesylate in 3 ml of methanol was added. The reaction mixture was stirred at room temperature for 1 hour, diluted with 5 ml of water, acidified with 10% hydrochloric acid, and extracted with methylene chloride (3×6 ml). The combined extracts were washed with brine (5 ml), dried and evaporated in vacuo. The residue was purified by thin layer chromatography, using hexane-ethyl acetate (95:5) as gradient, to afford the title compound, as an oil.

Provenance & Evidence