Abstract
Direct oxidation of eugenol has been done using potassium permanganate. This research attempts to produce benzyl carboxylic acid, an important intermediate reactant for isoflavone synthesis, directly by breaking the p bond of allillic group attached to eugenol. The oxidation procedures were adopted from Wahyuningsih and Kusumaningsih anetol oxidation reactions. There were three modifications done i.e. one polar system of the oxidation environment, variation of time of reflux and temperature. Eugenol was firstly diluted in water by converting to its salt type and then oxidized using KMnO4 at 75 oC for 4 hours. The expected acid was separated by acidifying using sulfuric acid.The result showed that direct oxidation of eugenol using modified method of Wahyuningsih gave only a vicinal diol which undergoes polymerization into product in 80% yield with 83% purity. However, variation of time of reflux of Wahyuningsih method showed the same result with Kusumaningsih method as brown oily viscous liquid. The product was only 38% purity.
Highlights
Isoflavone is one of secondary metabolic compounds paying attention intensively from researchers
The conversion can be done by oxidation of the terminal alkenes group of eugenol
This method will be the simplest way for the synthesis of important intermediate compound of daidzein derivate inasmuch as many researcher follow long steps of synthesis i.e. involving three additional steps, halidation, nitrilation and hydrolysis (Whalley, 2000)
Summary
Isoflavone is one of secondary metabolic compounds paying attention intensively from researchers. Retro-synthesis analysis of daidzein structure gives resorcinol and benzyl carboxylic acid derivate as the precursors (Figure 1.) The conversion can be done by oxidation of the terminal alkenes group of eugenol This method will be the simplest way for the synthesis of important intermediate compound of daidzein derivate inasmuch as many researcher follow long steps of synthesis i.e. involving three additional steps, halidation, nitrilation and hydrolysis (Whalley, 2000). Method In a 100 ml of Beaker glass was placed 0.03 mole of 97% eugenol, 10 ml of water and several mililiter of 10% sodium hydroxide was added drop wise while the solution is being stirred. The residue was analyzed using GCMS, FTIR (KBr disc) and 1H-NMR spectroscopy (60 MHz, CDCl3)
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