Sintesis 3-Benzoil-7-hidroksiflavon dari Resorsinol

Abstract

Flavonoid is the most abundant naturally-occuring polyphenolic compound with C6-C3-C6 carbon skeleton. Flavones is a group of flavonoid having a broad bioactivity spectrum. In this experiment, 3-benzoyl-7-hydoxyflavone was successfully synthesized via 2-steps from resorcinol. In the first step, resorcinol was acetylated with AcOH/ZnCl2 producing resacetophenone with 89% yield. Subsequently, benzoylation and rearrangement of resacetophenone using 2 equivalent of benzoyl chloride and 7 equivalent of K2CO3 in acetone produced 3-benzoyl-7-hydroxyflavone with 62% yield. Synthesis of 3-benzoyl-7-hydroxyflavone from resorcinol provided evidence for new reaction mechanism of flavon formation without Baker-Venkataraman rearrangement proposed by several previous researchers. All products in this study has been characterized spectroscopically.