The solid phase synthesis of monoester monoamides and monoester monoalcohols from symmetrical diacid chlorides

Abstract

A 2% crosslinked divinylbenzene–styrene copolymer, incorporating benzyl alcohol groups, was used to monoprotect the symmetrical diacid chlorides, ClOC(CH 2 ) n COCl (where n = 2, 3, 4, and 8), terephthaloyl chloride and isophthaloyl chloride. Subsequent reaction of the resulting polymer-bound monoester monoacid chloride with aniline, benzylamine, dimethylamine, tert-butylamine, or ammonia yielded polymer-bound monoester monoamides, which on base cleavage and esterification gave monoester monoamides inhighyield. Borohydride reduction of polymer-bound sebacoyl chloride, terephthaloyl chloride, and isophthaloyl chloride gave their respective polymer-bound monoester monoalcohols, which on base cleavage from the polymer and esterification yielded the monoester monoalcohols in good yield along with some recovered dimethyl esters of the respective starting diacid chlorides.