Methanol → Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (900 g, 7.56 mol) is added dropwise to methanol (1977 g, 61.72 mol) at 20° C. over a period of 1.5 hours, maintaining the temperature between 15°-25° C. with an ice bath. The cooling bath is removed and 5-chlorosalicylic acid (1000 g, 5.8 mol) added in one portion, then slowly heated to reflux. On completion of the reaction the solution is cooled to -5° C. for 1 hour. The methyl 5-chlorosalicylate is filtered, washed with cold methanol (150 ml) and dionized water (2×1 L). The solid is dried under house vacuum at 30° C. for 24 hours to give methyl 5-chlorosalicylate; m.p. 44°-46° C.

Provenance & Evidence