SYNTHESIS 7-HYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL

Andi Hairil Alimuddin; Muhammad Idham Darussalam Mardjan; Sabirin Matsjeh; Chairil Anwar; Mustofa Mustofa; Eti Nurwening Sholikhah

doi:10.22146/ijc.21404

SYNTHESIS 7-HYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL

https://doi.org/10.22146/ijc.21404

Andi Hairil Alimuddin^(1*), Muhammad Idham Darussalam Mardjan⁽²⁾, Sabirin Matsjeh⁽³⁾, Chairil Anwar⁽⁴⁾, Mustofa Mustofa⁽⁵⁾, Eti Nurwening Sholikhah⁽⁶⁾

(1) Student of Doctorate Program, Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Gadjah Mada
(2) Magister Program Student, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada Sekip Utara, Yogyakarta 55281
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada Sekip Utara, Yogyakarta 55281
(5) Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta
(6) Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta
(*) Corresponding Author

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.

Keywords

Eugenol; isoflavone; deoxybenzoin intermediate

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DOI: https://doi.org/10.22146/ijc.21404