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Journal > Indonesian Journal of Chemistry > SYNTHESIS OF 5,7-DIHYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL

 

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Indonesian Journal of Chemistry
Vol 11, No 3 (2011)
SYNTHESIS OF 5,7-DIHYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL
Alimuddin, Andi Hairil ( Student of Doctorate Program, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta)
Matsjeh, Sabirin ( Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta, Jl. Sekip Utara, Yogyakarta)
Anwar, Chairil ( 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)
Article Info   ABSTRACT
Published date:
20 Dec 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.
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