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

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SYNTHESIS OF 5,7-DIHYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL Andi Hairil Alimuddin; Sabirin Matsjeh; Chairil Anwar; Mustofa Mustofa
Indonesian Journal of Chemistry Vol 11, No 3 (2011)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (261.036 KB) | DOI: 10.22146/ijc.21385

Abstract

Synthesis of 5,7-dihydroxy-3',4'-dimethoxyisoflavone from eugenol as isolated product of clove leaves oil had been done. Eugenol was firstly converted into 3,4-dimethoxybenzyl cyanide via several stages of reaction. Hoeben-Hoesch reaction of 3,4-dimethoxybenzyl cyanide with phloroglucin produced 3,4-dimethoxybenzyl-2',4',6'-trihydroxyphenyl ketone (deoxybenzoin intermediate) in 58% yield. Eventually, cyclization of the intermediate with reagents of BF3.OEt2/DMF/POCl3 yielded 5,7-dihydroxy-3',4'-isoflavone in 88% yield.
Co-Authors Chairil Anwar Mustofa Mustofa Sabirin Matsjeh