Formaldehyde → 1-(4-Chlorophenyl)-2-butyn-1-ol

Participants

Reaction Steps

Dissolve 150.6 g (1.00 mole) of 1-chloro-4-(2-propynyl)benzene in 600 ml of anhydrous ether under N2 atmosphere with stirring at dry ice/acetone temperature. Add dropwise a solution of 400 ml of n-butyllithium (2.5M in hexane) (1.00 mole). Stir for an additional 30 minutes after completion of addition. Add 31 g (1.00 mole) of paraformaldehyde. Stir the mixture at dry ice/acetone temperature for 1 hour, and allow to warm to room temperature. Follow the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride). At the completion of the reaction, add 400 ml of saturated aqueous sodium chloride, separate layers, and extract aqueous layer with ether (2×100 ml). Wash the combined ether solutions with water, dry over magnesium sulfate and evaporate. Triturate the oil residue with petroleum ether to provide the title compound.

Provenance & Evidence