Sintesis 1-(2-hidroksifenil)-3-fenilpropana-1,3-dion dari o-hidroksiasetofenon dan benzoil klorida

Abstract

Flavonoid is the most abundant naturaly-occuring polyphenolic compound which has C6-C3-C6 carbon skeleton. Flavone is a group of flavonoid with wide bioactivity spectrum. It is widely distributed in higher plants. Its bioactivities include antioxidant, HIV-1 proteinase inhibitor, strong and selective apoptotic inducer in human colon cell, and ligand for BDZ-R receptor. One of the important and widely applicable flavones synthesis route is through 1-(2-hydroxyphenyl)-3- phenylpropane-1,3-dione (1,3-diketone) acid-catalyzed oxidative cyclization. In this study, 1,3-diketone has been successfully synthesized via four-step route. In the first step, phenol was acetylated with 74–95% yields. Subsequently, phenyl acetate was converted to o-hydroxyacetophenone (o-HAP) with 34% yield via AlCl3-catalyzed Fries rearrangement. Benzoylation of o-HAP followed by Baker- Venkataraman rearrangement of the ester product using KOH in pyridine finally produced 1,3-diketone. The third and fourth steps yield were 27–44% and 82– 85%, respectively. All products in this study have been characterized spectroscopically. Melting point characterization were also conducted to the solid products.