Improved Synthesis of 2',6'-Dihydroxy-3,4-dimethoxy Chalcone by Grinding Technique to Synthesize 5-Hydroxy-3',4'-dimethoxy Flavone

https://doi.org/10.22146/ijc.21255

Elfi Susanti VH(1*), Sabirin Matsjeh(2), Mustofa Mustofa(3), Tutik Dwi Wahyuningsih(4)

(1) Department of Chemistry FKIP Universitas Sebelas Maret, Ir Sutami 36A Surakarta 57126
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara Yogyakarta 55281
(3) Faculty of Medicine, Universitas Gadjah Mada, Jl. Sekip Utara Yogyakarta 55281
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara Yogyakarta 55281
(*) Corresponding Author

Abstract


5-hydroxy-3',4'-dimethoxy flavone can be efficiently synthesized in two steps via the formation of 2',6'-dihydroxy-3,4-dimethoxy chalcone with good results. 2',6'-dihydroxy-3,4-dimethoxy chalcone as reactants for synthesis of flavones was prepared through Claisen-Schmidt condensation reaction between 2,6-dihydroxyacetophenones,3,4-dimethoxybenzaldehyde and solid NaOH in mortar for 15 min. The yield of the product (70%) is higher than conventional method (65%). This chalcone then oxidatively cyclized with iodine to form 5-hydroxy-3',4'-dimethoxy flavone (yield 62%). Compounds synthesized were characterized by spectroscopic (IR, 1H-NMR, and 13C-NMR).

Keywords


chalcone; flavone; Claisen-Schmidt; grinding

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DOI: https://doi.org/10.22146/ijc.21255

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