2-Methoxybenzoic acid → 2-Methoxybenzoyl chloride

Participants

Reaction Steps

A mixture of 5 g of o-anisic acid and 10 ml of thionyl chloride was heated at 100° for about fifteen minutes. Excess thionyl chloride was removed under reduced pressure to give crude o-anisoyl chloride. The title compound was then prepared from 0.5 g of the title product of Example 3 using the general method of Example 14. Before recrystallization, however, the resultant solid was dissolved in water, made basic with 10% aqueous sodium carbonate, and extracted into dichloromethane. The extract was concentrated to dryness and the residue was purified by column chromatography on silica gel. Fractions containing the free base of the title compound were converted to the hydrochloride as in Example 2. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Provenance & Evidence