Hydrochloric Acid → 4-Methyloxybenzyl chloride

Participants

Reaction Conditions

Reaction Steps

A solution comprising 108.1 grams of anisole in 450 ml of benzene was cooled to 2° C. and then saturated with gaseous hydrogen chloride for a period of 3 hours at a maximum temperature of 5° C. Then 38.6 grams of paraformaldehyde was added thereto at 20° C. and, following the addition, the reaction mixture was heated to 45° C. and maintained thereat for 1 hour and again cooled to 20° C. Following, gaseous hydrogen chloride was introduced for an additional 5 hours. Next, the aqueous layer was separated and the benzene solution washed with a saturated solution of calcium chloride in eight 150 ml portions and dried over magnesium sulfate. The residue was distilled in vacuum to yield 102.7 grams (65.7%) of 4-methoxybenzyl chloride, b.p. 108°-110° C./12 Torr.

Provenance & Evidence