Dimethyl Sulfate → Benzoic acid, 2,3,4,5-tetrachloro-6-cyano-, methyl ester

Participants

Reaction Steps

A reaction vessel containing 30 ml of water and 60 ml of methyl ethyl ketone is charged with 16.15 g of the dry potassium salt of 3,4,5,6-tetrachloro-2-cyanobenzoic acid. With stirring, the mixture is heated to 72°-74° C. and 9.45 g of dimethyl sulfate are added dropwise at the same temperature to the resultant suspension, while keeping the pH at 6-8 by the gradual addition of 30% potassium hydroxide solution. The reaction mixture is kept under reflux for 2 hours and the aqueous layer is then separated. The organic layer is completely evaporated, affording 12.4 g of methyl 3,4,5,6-tetrachloro-2-cyanobenzoate with a melting point of 82°-83° C.

Provenance & Evidence