Water → 2,3-Dihydroxypropyl 4-(n-hexadecylamino)benzoate

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Reaction Steps

A solution of 3.8 g. sodium 4-(n-hexadecylamino)benzoate, 3.7 g. of epichlorohydrin, and 0.7 ml. of water in hexamethylphosphoramide is heated to 90° C. for 5 hours. An additional 0.7 ml. of water is added, followed by 1 ml. of 1N sulfuric acid. The reaction mixture is cooled after 11/2 hours. After adding dimethoxyethane and benzene, the organic layer is separated and washed with water. The solvent is removed in vacuo to give a white solid which is recrystallized from 15 ml. of acetonitrile to yield 2,3-dihydroxypropyl 4-(n-hexadecylamino)benzoate. If this material contains any of the intermediate 2,3-epoxypropyl 4-(n-hexadecylamino)benzoate, it is removed by chromatography on silica gel.

Provenance & Evidence