3-(Dimethylamino)phenol → [3-(3-Dimethylaminophenoxy)acetonylidene]triphenylphosphorane

Participants

Reaction Steps

n-Butyl-lithium (3.85 ml. of a 1.3 M solution in hexane) was added to a solution of 3-dimethylaminophenol (685 mg.) in dimethoxyethane (20 ml.) at -70° C. under an atmosphere of nitrogen. The solution was allowed to warm to room temperature, a solution of 3-iodoacetonylidene-triphenylphosphorane (2.22 g.) in benzene (100 ml.) was added, and the mixture was heated under reflux for 2 hours. The mixture was then diluted with toluene (100 ml.), washed with water (2×50 ml.) and dried, the solvents were evaporated and the residue was triturated with ether to give [3-(3-dimethylaminophenoxy)acetonylidene]triphenylphosphorane, m.p. 110°-115° C.

Provenance & Evidence