Hydrochloric Acid → Methyl 2-[2-(chloromethyl)phenyl]acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.0 g (6.75 mmol) of 3-isochromanone in 10 ml of toluene was added 2.68 ml (29.7 mmol) of dichloromethyl methyl ether, and the mixture was stirred at 60° C. for 24 hours. After cooling to room temperature, a mixed solution of 3 ml of methyl alcohol and 1.1 ml of pyridine was added thereto, followed by further stirring at room temperature for 24 hours. To the reaction mixture was added 20 ml of 1N hydrochloric acid, followed by extraction with 20 ml of ethyl ether. The combined ether extract was washed with two 20 ml portions of 1N hydrochloric acid. Ethyl ether was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 1.034 g (yield: 77.1%) of pure methyl 2-(chloromethyl)phenylacetate.

Provenance & Evidence