Sintesis Flavon dari Fenol dan Benzoil Klorida

Abstract

Flavone is a class of flavonoid, commonly found in plants with wide bioactivity spectrum. A widely used flavone synthesis route is through acidcatalyzed oxidative cyclization of β-diketone. In this study, unsubstituted flavone had been synthesized via 5-step from phenol, with 22% yield and successfully increased the yield of previous study on Fries rearrangement of phenyl acetate and benzoylation of o-HAP steps. Phenol was acetylated resulting 93% phenyl acetate. AlCl3-catalyzed Fries rearrangement in 1.5 hour and at 120 °C converted phenyl acetate into o-hydroxyacetophenone (o-HAP) with 40% yield. AlCl3 as catalyst produced o-HAP with higher and reproducible yield compared with BF3·Et2O and ZnCl2. Benzoylation of o-HAP followed by Baker-Venkataraman rearrangement of the ester product using KOH in dried pyridine produced β-diketone 1-(2- hydroxyphenyl)-3-phenylpropane-1,3-dione. The yield of ester and β-diketone were 71% and 85%, respectively. Finally, oxidative cyclization of β-diketone with sulphuric acid as catalyst produced 99% of flavone. The flavone product had been characterized spectroscopically and its melting point as well.