Hydrochloric Acid → HCID 13662991, compound

Participants

Reaction Steps

5-Hydroxymethyl-3-methylbenzo[b]thiophene-2-carboxylic acid (4.4 g.) was dissolved in methanol (150 ml.) and the solution was saturated with hydrogen chloride gas. It was then heated under reflux for 4 hours and cooled. The solid which crystallized out was filtered off and dried. The product (3.54 g.) was shown by n.m.r. to consist of a mixture of 5-chloromethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester (65%) and 5-methoxymethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester. The product was chromatographed on silica gel. Elution with toluene first gave 5-chloromethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester, m.p. 115°-116° C. (from petrol b.p. 40°-60° C.).

Provenance & Evidence