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

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

doi:10.22146/ijc.21385

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

https://doi.org/10.22146/ijc.21385

Andi Hairil Alimuddin^(1*), Sabirin Matsjeh⁽²⁾, Chairil Anwar⁽³⁾, Mustofa Mustofa⁽⁴⁾

(1) Student of Doctorate Program, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta, Jl. Sekip Utara, Yogyakarta
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta, Jl. Sekip Utara, Yogyakarta
(4) Pharmacology Division, Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta, Jl. Farmaco Yogyakarta
(*) Corresponding Author

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.

Keywords

eugenol; isoflavone; deoxybenzoin intermediate

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DOI: https://doi.org/10.22146/ijc.21385