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

Participants

Reaction Steps

A solution of 3.6 g. of 4-(n-hexadecylamino)benzoic acid and 1.0 g. of 2,3-epoxypropan-1-ol in 100 ml. of hexamethylphosphoramide is heated at 90° C. for 8 hours. After addition of ether and water, the ether layer is separated and the ether extraction repeated several times. Following evaporation of the ether extracts, the mixture of starting material and desired 2,3-dihydroxypropyl ester is separated by chromatography on silica gel and recrystallized from acetonitrile.

Provenance & Evidence