HCID 15685334, compound → 4-(Hexadecylamino)benzoic acid

Participants

Reaction Steps

p-Hexadecylaminobenzoic acid (2.0 g.) is dissolved in 20 ml. of dry tetrahydrofuran, and to this is added portionwise at room-temperature 0.5 g. of lithium aluminum hydride. The mixture is stirred at room temperature for 3 hours, and then is quenched with 10% aqueous ammonium chloride solution. The mixture is filtered, and the filtrate is evaporated in vacuo to provide a yellow solid. The residue is extracted several times with methylene chloride and the extracts are evaporated in vacuo to give a white solid. Recrystallization from hexane gave the product of the Example, m.p. 74°-75° C. Replacement of p-hexadecylaminobenzoic acid with p-octylaminobenzoic acid, p-nonylaminobenzoic acid, p-decylaminobenzoic acid, p-undecylaminobenzoic acid, p-dodecylaminobenzoic acid, p-tridecylaminobenzoic acid, p-(14-methylpentadecyl)aminobenzoic acid, p-pentadecylaminobenzoic acid, p-heptadecylaminobenzoic acid, p-octadecylaminobenzoic acid, and nondecylaminobenzoic acid provide respectively, p-octylaminobenzyl alcohol, p-nonylaminobenzyl alcohol, p-decylaminobenzyl alcohol, p-undecylaminobenzyl alcohol, p-dodecylaminobenzyl alcohol, p-tridecylaminobenzyl alcohol, p-pentadecylaminobenzyl alcohol, p-(14-methylpentadecyl)aminobenzyl alcohol, p-heptadecylaminobenzyl alcohol, p-octadecylaminobenzyl alcohol and p-nonadecylaminobenzyl alcohol.

Provenance & Evidence