S. Matsjeh, C. Anwar, E. N. Solikhah
Jul 1, 2017
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Journal
Materials Science Forum
Abstract
Some Isoflavones 7-hydroxy-3',4'-dimethoxyisoflavone (2), 7,3',4'-trimethoxyisoflavone (3) and 7-O-acetyl-3',4'-dimethoxyisoflavone (4) have been synthesized through cyclization reaction of deoxybenzoine using a reagent mixture BF3.Et2O , DMF and POCl3. The DMF reagent was added aiming to add one carbon to form isoflavone 1. The deoxybenzoine (3,4-dimethoxybenzyl-2', 4'-dihydroxyphenylketone, (1) was synthesized by reacting 3,4-dimethoxy benzyl carboxylic acid and resorcinol through Friedel Craft acylation using a Lewis acid (BF3) as a catalyst. The isoflavones 1 was converted into isoflavone 2 via methylation reaction using dimethylsulfate (DMS) and K2CO3 and conversions into isoflavone3 through acetylation reaction using acetylchloride. The results were analyzed using FTIR, GC-MS and 1H NMR spectrometers. Deoxybenzoine derivatives of 3,4-dimethoxybenzyl-2',4'-dihydroxy phenylketone was yielded in 57% with m.p 171-172 °C. The isoflavone 1, 2 and 3 was produced in 58, 52 and 53 % yield, respectively.