Benzyl Alcohol → Benzyl chloromethyl ether

Participants

Reaction Steps

A mixture of 216.28 g. of benzyl alcohol, 61.44 g. of paraformaldehyde, 481.6 g. of anhydrous magnesium sulfate and 1200 ml. of methylene chloride is cooled to a temperature of between -50° to -55°C in a dry ice-acetonitrile bath, and the stirred cold solution is saturated with an anhydrous hydrogen chloride gas. The reaction mixture is kept at -50° to -55°C for 10 minutes further, and then the excess of hydrogen chloride is eliminated by passing a stream of nitrogen during 30 minutes. The reaction mixture is filtered and the solid material washed well with pentane, and the combined filtrates are evaporated to dryness at a temperature below 30°C, to produce an oil which is distilled under reduced pressure to yield chloromethyl benzyl ether.

Provenance & Evidence