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

Andi Hairil Alimuddin | Zendy; Muhammad Idham Darussalam Mardjan | Zendy; Sabirin Matsjeh | Zendy; Chairil Anwar | Zendy; Mustofa Mustofa | Zendy; Eti Nurwening Sholikhah | Zendy

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

Author(s) -

Andi Hairil Alimuddin,

Muhammad Idham Darussalam Mardjan,

Sabirin Matsjeh,

Chairil Anwar,

Mustofa Mustofa,

Eti Nurwening Sholikhah

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.21404

Subject(s) - chemistry , eugenol , yield (engineering) , acylation , methyl eugenol , reagent , ketone , organic chemistry , friedel–crafts reaction , raw material , medicinal chemistry , botany , catalysis , materials science , pest analysis , metallurgy , biology , tephritidae

Eugenol from the isolation of clove leaves oil had been utilized in the synthesis of 7-hydroxy-3’,4’-dimethoxyisoflavone 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.

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