Water → 5-Chloro-2,4-dihydroxy-3-propylbenzoic acid methyl ester

Participants

Reaction Steps

A solution of 2.1 g (0.01 mol) of 2,4-dihydroxy-3-propylbenzoic acid methyl ester and 1.6 g (0.012 mol) of N-chlorosuccinimide in 50 mL of carbon tetrachloride was stirred at reflux for 9.5 hours. Additional N-chlorosuccinimide (1.6 g) was added and reflux was continued for 17 hours. 0.8 g of N-chlorosuccinimide was added and reflux was continued for 8 hours. Water was added. The organic layer was separated and washed with sodium thiosulfate solution, sodium bicarbonate solution, dried and concentrated under reduced pressure to give 5-chloro-2,4-dihydroxy-3-propylbenzoic acid methyl ester. Recrystallization from hexane gave analytically pure material, mp 75°-76°.

Provenance & Evidence