Water → p-Toluic acid, 3,5-dimethylphenyl ester

Participants

Reaction Steps

p-Toluoyl chloride (154 g.) was added during 30 minutes to a solution of 3,5-dimethylphenol (122 g.) in anhydrous pyridine (200 ml.), with stirring. The temperature rose to 80° C. The mixture was stirred and heated on the steambath for 3 hours, and was then cooled and stirred with diethyl ether (500 ml.) and water (2000 ml.). The organic layer was separated, and the aqueous layer was further extracted with diethyl ether (3×250 ml.). The combined ether solutions were washed with N aqueous sodium hydroxide solution to remove unchanged starting materials and with 2 N hydrochloric acid to remove pyridine, and finally with water. The solution was dried over anhydrous sodium sulphate and evaporated in vacuo, and the residue was recrystallised from light petroleum (b.p. 40°-60° C.; 550 ml.) to give 3.5-dimethylphenyl p-toluate (203 g.). m.p. 55°-57° C.

Provenance & Evidence