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

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)

Indonesian Journal of Chemistry
Vol 11, No 3 (2011)

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.