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

Andi Hairil Alimuddin | Zendy; Sabirin Matsjeh | Zendy; Chairil Anwar | Zendy; Mustofa Mustofa | Zendy

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

Author(s) -

Andi Hairil Alimuddin,

Sabirin Matsjeh,

Chairil Anwar,

Mustofa Mustofa

Publication year - 2011

Publication title -

indonesian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.273

H-Index - 14

eISSN - 2460-1578

pISSN - 1411-9420

DOI - 10.22146/ijc.21385

Subject(s) - eugenol , chemistry , yield (engineering) , ketone , reagent , cyanide , methyl eugenol , organic chemistry , medicinal chemistry , botany , materials science , pest analysis , metallurgy , biology , tephritidae

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. HoebenHoesch 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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