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Andi Hairil Alimuddin
Student of Doctorate Program, Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Gadjah Mada
Chemical Engineering, Chemistry & Bioengineering Chemistry

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SYNTHESIS 7-HYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL Andi Hairil Alimuddin; Muhammad Idham Darussalam Mardjan; Sabirin Matsjeh; Chairil Anwar; Mustofa Mustofa; Eti Nurwening Sholikhah
Indonesian Journal of Chemistry Vol 11, No 2 (2011)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (233.66 KB) | DOI: 10.22146/ijc.21404

Abstract

Eugenol from the isolation of clove leaves oil had been utilized in the synthesis of 7-hydroxy-3',4'-dimethoxy-isoflavone based on deoxybenzoin intermediate. The raw material was firstly converted into methyleugenol using DMS (89.87%). Secondly, methyl eugenol was oxidized using KMnO4 to produce 3,4-dimethoxybenzyl carboxylic acid (21%). Friedel-Craft acylation of it with recorcinol produced 3,4-dimethoxybenzyl-2',4'-dihydroxyphenyl ketone (deoxybenzoin intermediate) in 78% yield. Eventually, cyclization of the intermediate with reagents of BF3.OEt2/DMF/POCl3 yielded 7-hydroxy-3',4'-isoflavone in 85% yield.
Co-Authors Chairil Anwar Eti Nurwening Sholikhah Muhammad Idham Darussalam Mardjan Mustofa Mustofa Sabirin Matsjeh