Dimethyl Sulfoxide → Benzoic acid, 3-amino-4-chloro-, dodecyl ester

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Reaction Conditions

Reaction Steps

17.2 g (0.1 mol) of 3-amino-4-chlorobenzoic acid was added to 50 ml of dimethylsulfoxide.. Then 13.8 g (0.1 mol) of potassium carbonate was added to the solution obtained above, and the resulting mixture was stirred in the temperature range of from 20 to 30° C. for 30 min. 22.5 g (0.11 mol) of dodecyl chloride was poured into the solution thus obtained, and the resulting solution was heated to 100° C., and allowed to react at the temperature for 1 hour. After completing the reaction, 50 ml of ethyl acetate, and 50 ml of water were added to the reaction mixture, and the organic layer obtained was separated, concentrated, diluted with 100 ml of methanol, and then cooled to precipitate crystals. The crystals were separated by filtration, and then dried to obtain 32.3 g (yield 95%) of the desired product. Purity 99% or higher. Melting point 58.0-59.2° C. A result of the elemental analysis of this sample was as follows:

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