Sintesis Krisin dari Floroglusinol

Abstract

Flavone is a class of flavonoid, widely distributed in vascular plants. Flavones containing hydroxyl groups at 5 and 7 position are quite important regarding their biological activities and their abiquity in nature. Flavone having hydroxyl groups only at position 5 and 7 or 5,7-dihydroxyflavone is known as chrysin. In this study, crude chrysin had been successfully synthesized in 3 steps from phloroglucinol as starting material. Phloroglucinol was acetylated with acetonitrile and HCl gas, resulting phloroacetophenone amount to 74%. Phloroacetophenone benzoylation with 4.5 equivalents of benzoyl chloride produced tribenzoyl phloroacetophenone in 103–107% of yield and the subsequent Baker-Venkataraman rearrangement of the ester by using KOH in dried pyridine produced crude chrysin, with conversion percentage of 71.62%. All synthetic products had been characterized by melting point and spectroscopically.