Methanol → 2-Chloro-6-chloromethylnaphthalene

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (99.4 g.) is added dropwise at 0° C. during 1 hour to a stirred suspension of the 6-chloro-2-hydroxymethylnaphthalene (96.3 g.) in a mixture of pyridine (50.0 g.) and chloroform (2 l.). The mixture is stirred for 1 hour at 20° C., then treated dropwise with methanol (60 ml.) and stored for 18 hours. The solution is washed with water, 3N-hydrochloric acid, and water again, dried with magnesium sulphate and evaporated. The residue is crystallised from light petroleum (b.p. 80°-100° C.) to give 2-chloromethyl-6-chloronaphthalene (101 g.) m.p. 107°-110° C. raised to 110°-111° C. by further crystallisation.

Provenance & Evidence