3-Hydroxybenzoic Acid → HCID 18801618, compound

Participants

Reaction Steps

A solution of potassium hydroxide (1.32 g; 85% pellets) in dry methanol (25 ml) was treated at room temperature with metahydroxybenzoic acid (1.38 g) to give a solution. This was stirred for 30 minutes and then coevaporated with added toluene to give a white solid. The solid was dispersed in dry dimethylsulphoxide (10 ml.) Anhydrous potassium carbonate (0.5 g) and 2-chloro-5-trifluoromethylpyridine (1.82 g) were added, and the solution stirred. After 64 hours, water (100 ml) was added. The mixture was extracted with chloroform, filtered and brought to pH 1 with concentrated hydrochloric acid. The solid which precipitated was washed with water and dried to give 2-(3-carboxyphenoxy)-5-trifluoromethylpyridine (2.4 g) (m.p. 146° C.).

Provenance & Evidence