Development of an efficient method for preparation of 1,3,5-trihydroxyisocyanuric acid(THICA)and its use as aerobic oxidation catalyst

摘要

1,3,5-Trihydroxyisocyanuric acid(THICA),which serves as an efficient radical-producing catalyst from hydrocarbons,was successfully prepared by two methods.The reaction of 0-benzylhydroxyamine with phenyl chloroformate gave formbenzyloxycarbamic acid phenyl ester of which subsequent treatment with dimethylaminopyridine(DMAP)produced 1,3,5-tribenzyloxyisocyanurate leading to THICA by hydrogenation with H_2 on Pd/C.The other method involved the direct synthesis of 1,3,5-tribenzyloxyisocyanurate from O-benzylhydroxyamine and diphenyl carbonate.The aerobic oxidation of p-methylanisole catalyzed using THICA as a key catalyst afforded p-anisic acid in almost quantitative yield(>99%).