Ammonia → 4,4-Diphenyl-1-butene

Participants

Reaction Steps

A solution of 1.5 1. of liquid ammonia containing 19.5 g. of sodium amide was stirred while a solution of 84.1 g. of diphenylmethane dissolved in 200 ml. of diethyl ether was added dropwise over about 30 minutes. The reaction mixture was stirred for 45 minutes after the addition was completed. A solution of 60.5 g. of 3-bromo-1-propene in 50 ml. of diethyl ether was then added to the reaction mixture, after which time the mixture was stirred for twelve hours. A saturated aqueous solution of ammonium chloride was then added to the reaction mixture, followed by the addition of 500 ml. of water. The product was extracted from the aqueous reaction mixture into diethyl ether. The ethereal extracts were combined, washed, and dried. Evaporation of the solvent under reduced pressure provided 93.2 g. of the product as an oil. Distillation of the crude oil afforded 4,4-diphenyl-1-butene, B.P. 95°-98° C 0.10 torr.

Provenance & Evidence