3-Chloro-1,2-propanediol → 2,3-Dihydroxypropyl 4-(n-hexadecylamino)benzoate

Participants

Reaction Conditions

Reaction Steps

A solution of 7.20 g of 4-(n-hexadecylamino)benzoic acid in 25 ml of hexamethylphosphoramide is added to a stirred mixture of 0.800 g of sodium hydride (57% in mineral oil) and 25 ml of hexamethylphosphoramide. The soluion which forms after one hour is treated with 11.0 g of 1-chloro-2,3-propanediol and is then stirred at 60° C for 18 hours. Dilution with water followed by filtration affords a white solid which is crystallized from ethanol to yield 2,3-dihydroxypropyl 4-(n-hexadecylamino)benzoate melting at 112°-113° C.

Provenance & Evidence