1-(4-(Propan-2-yloxy)phenyl)ethan-1-one → 1-Isopropoxy-4-(1-hydroxy-1-methylethyl)benzene

Participants

Reaction Steps

Reaction of 1-isopropoxy-4-acetylbenzene with methyl magnesium bromide afforded 1-isopropoxy-4-(1-hydroxy-1-methylethyl)benzene. A solution of 35 g. of 1-isopropoxy-4-(1-hydroxy-1-methylethyl)benzene in 65 ml. of ethyl alcohol and 300 ml. of liquid ammonia was stirred while 5 g. of Lithium metal in the form of small pieces was added portionwise over thirty minutes. The reaction mixture was stirred for an additional thirty minutes, and then was diluted with 150 ml. of toluene and 35 g. of ammonium chloride. The reaction mixture was stirred at room temperature for twelve hours, and then was further diluted with 200 ml. of water. The aqueous layer was separated and extracted with 100 ml. of fresh toluene. The toluene layers were combined, washed with water, dried, and concentrated by evaporation under reduced pressure. Distillation of the residue provided 22.8 g. of 1-isopropoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene. B.P. 85°-87° C. at 0.02 torr.

Provenance & Evidence