Hydrochloric Acid → p-(Trifluoromethoxy)benzaldehyde

Participants

Reaction Steps

A solution of 4-trifluoromethoxyiodobenzene (39.28 g.) in anhydrous diethyl ether (200 ml.) was added dropwise at -70° C. to n-butyl-lithium (96 ml. of a 1.6M solution in hexane) over 25 minutes. The solution was stirred for 30 minutes, and then dimethylformamide (14.83 g.) and anhydrous ether (50 ml.) were added over 15 minutes. After 1 hour, the solution was allowed to warm to -20° and was then hydrolysed by the addition of 3N hydrochloric acid (150 ml.). The organic layer was separated, and the aqueous layer was extracted twice with diethyl ether. The ether extracts were combined, washed with water, dried over magnesium sulphate and filtered, and the solvent was evaporated to give a yellow oil. Distillation of this oil gave 4-trifluoromethoxy benzaldehyde, b.p. 75°-7°/8 mm. of mercury, pressure.

Provenance & Evidence