Phenol → 5-Chloro-2-(phenoxymethyl)benzoic acid

Participants

Reaction Steps

Sodium hydride (1.0 mol) is suspended in about 300 ml. of dimethylformamide and phenol (1.0 mol) in about 200 ml. of dimethylformamide is added dropwise, keeping the reaction temperature around 25° C. The mixture is stirred until hydrogen evolution is completed. 6-Chlorophthalide (1.0 mol) in about 250 ml. of dimethylformamide is then added slowly. The resulting mixture is refluxed for 2 hours and allowed to stand at room temperature overnight. The reaction mixture is diluted with ice/water and extracted several times with ether. The aqueous fraction is acidified with dilute hydrochloric acid and extracted with ether. The ether is dried and concentrated to a gummy solid which is recrystallized from a minimum volume of alcohol to give 2-phenoxymethyl-5-chlorobenzoic acid, m.p. 149°-155° C.

Provenance & Evidence