Water → 3-(Carboxymethyl)-2-chlorobenzoic acid

Participants

Reaction Conditions

Reaction Steps

Concentrated sulfuric acid (60 mL) was added dropwise to ice-cold water (75 mL) and the resulting solution was added to 2-chloro-3-(cyanomethyl)benzoic acid [Aromatic Intermediate 11, step b] (14 g). The resulting suspension was heated to reflux (165° C.) for 30 min during which the starting material dissolved and a new precipitate was observed. The reaction was allowed to cool and was diluted with water (250 mL) and extracted with ethyl acetate (3×500 mL). The combined organic phases were washed with water (250 mL) and brine (250 mL), then dried over magnesium sulphate and evaporated to give the subtitled compound as a white solid. Yield 13.7 g.

Provenance & Evidence