Synthesis of Hibiscetin
P Ramachandra Rao P Suryaprakasa Rao T R Seshadri
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A convenient method of preparing 2∶4-dihydroxy-ω∶3∶6-trimethoxyacetophenone (I) directly from 2∶6-dibenzyloxy-1∶4-dimethoxybenzene is described. By the condensation of (I) with the sodium salt and anhydride of trimethylgallic acid, 7-hydroxy-3∶5∶8∶3′∶4′∶5′-hexamethoxyflavone (II) is obtained. Methylation of (II) yields a heptamethyl ether (III) identical with heptamethyl hibiscetin. Demethylation of (II) gives rise to a heptahydroxy flavone (IV) which is found to be identical with hibiscetin in all its properties and reactions. The constitution of hibiscetin is therefore confirmed by synthesis as 3∶5∶7∶8∶3′∶4′∶5′-heptahydroxy flavone.
P Ramachandra Rao1 2 P Suryaprakasa Rao1 2 T R Seshadri1
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