SYNTHESIS OF 5,7-DIHYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL

Andi Hairil Alimuddin; Sabirin Matsjeh; Chairil Anwar; Mustofa Mustofa

doi:10.22146/ijc.21385

Indonesian Journal of Chemistry (Dec 2011)

SYNTHESIS OF 5,7-DIHYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL

Andi Hairil Alimuddin,
Sabirin Matsjeh,
Chairil Anwar,
Mustofa Mustofa

Affiliations

Andi Hairil Alimuddin: Student of Doctorate Program, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta
Sabirin Matsjeh: Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta, Jl. Sekip Utara, Yogyakarta
Chairil Anwar: Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta, Jl. Sekip Utara, Yogyakarta
Mustofa Mustofa: Pharmacology Division, Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta, Jl. Farmaco Yogyakarta

DOI: https://doi.org/10.22146/ijc.21385
Journal volume & issue: Vol. 11, no. 3
pp. 229 – 233

Abstract

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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.

Published in Indonesian Journal of Chemistry

ISSN: 1411-9420 (Print); 2460-1578 (Online)
Publisher: Department of Chemistry, Universitas Gadjah Mada
Country of publisher: Indonesia
LCC subjects: Science: Chemistry
Website: https://jurnal.ugm.ac.id/ijc/

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