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

Andi Hairil Alimuddin (Student of Doctorate Program, Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Gadjah Mada)
Muhammad Idham Darussalam Mardjan (Magister Program Student, 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 Sekip Utara, Yogyakarta 55281)
Chairil Anwar (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada Sekip Utara, Yogyakarta 55281)
Mustofa Mustofa (Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta)
Eti Nurwening Sholikhah (Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta)

Indonesian Journal of Chemistry
Vol 11, No 2 (2011)

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.