SYNTHESIS OF 5,7-DIHYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL
Andi Hairil Alimuddin, Sabirin Matsjeh, Chairil Anwar and 1 more
Indonesian Journal of Chemistry · 2011
doi:10.22146/ijc.21385 (opens in a new tab)
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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.
Abstract licence: CC BY-NC-ND
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