Hydrochloric Acid → 4-(Hexadecylamino)benzoic acid

Participants

Reaction Steps

27.4 g (0.2 mol) of 4-aminobenzoic acid, 11.2 g of KOH, 64 g (0.21 mol) of 1-bromohexadecane and 4.64 g (10 mmol) of hexadecyltributylphosphonium chloride were suspended in 250 ml of ethanol (96%) and the reaction mixture was stirred for 12 hours at reflux temperature. While the solution was still hot, there were added, drop by drop, 80 ml of conc. HCl and the reaction mixture was left to cool down to ambient temperature. Thereupon the precipitated product was separated on a suction filter, washed with water and dried. After the crystallization of the crude product from benzene, there was obtained the 4-(n-hexadecylamino)-benzoic acid, m.p. 107°-107° C., complete m.p. 122°-126° C., which could be optionally converted into its sodium salt.

Provenance & Evidence