Dimethyl Sulfate → 5-Chloro-o-anisic acid

Participants

Reaction Steps

To a solution of methyl 5-chlorosalicylate (20 g.) in acetone 110 ml.) was added 2 N sodium hydroxide (66 ml.) and dimethyl sulphate (13.86 g.). The mixture was stirred for 10 minutes, sodium hydroxide 33 ml., 2N) and dimethyl sulphate (6.93 g.) added, and the mixture was heated under reflux for 45 minutes. The product was then cooled, the acetone evaporated off, and the residue was taken up in ether. The ether was extracted with dilute sodium hydroxide, evaporated off, and the residue heated under reflux for 1 hour with 10 aqueous sodium hydroxide (100 ml.). The product was cooled and acidified. The precipitate acid was filtered off and recrystallized from ethanol-water to give 8 g., m.p. 80°-81° (45%) with a second crop of 0.8 g., m.p. 77°-79° (4.5%).

Provenance & Evidence