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

Full Text:

Full Text Pdf


References

[1] Belsare, D.P., Pal, S.C., Kazi, A.A., Kankate, R.S., and Vanjari, S.S., 2010, Int. J. ChemTech. Res., 2 (2), 1080–1089.

[2] Sandhar, H.K., Kumar, B., Prasher, S., Tiwari, P., Salhan, M., and Sharma, P., 2011, Int. Pharm. Sci., 1 (1), 25–41.

[3] Venkatesan, P., and Maruthavanan, T., 2011, Bull. Chem. Soc. Ethiop., 25 (3), 419–425.

[4] Mostahar, S., Katun, P., and Islam, A., 2007, J. Biol. Sci., 7 (3), 514–519.

[5] Murthy, Y.L.N., Viswanath, I.V.K., and Pandit, E.N., 2010, Int. J. ChemTech Res., 2 (2), 1097–1101.

[6] Theja, D., Choudary, T.P., Reddy, M.I, Avss, G., and Reddy, K.U., 2011, Int. J. Pharm. Pharm. Sci., 3(2), 51–54.

[7] Patil, C.B., Mahajan S.K., and Katti, S.A., 2009, J. Pharm. Sci. Res., 1 (3), 11–22.

[8] Xia, Y., Yang, Z.Y., Xia, P., Bastow, K.F., Nakanishi, Y., and Lee, K.H., 2000, Bioorg. Med. Chem. Lett., 10 (8), 699–701.

[9] Mandge, S., Singh, H.P., Gupta D., and Moorthy H.R., 2007, Trend Appl. Sci. Res., 2 (1), 52–56.

[10] Prasad, Y.R., Lakshmana, A.R., and Rambabu, R., 2008, E-J. Chem., 5 (3), 461–466.

[11] Nalwar, Y.S., Sayyed, M.A., Mokle, S.S., Zanwar, P.R., and Vibhute, Y.B., 2009, World J. Chem., 4 (2), 123–126.

[12] Susanti, E.V.H., Matsjeh, S., Wahyuningsih, T.D., Mustofa, and Redjeki, T., 2012, Indo. J. Chem., 12 (2), 146–151.

[13] Susanti, E.V.H., Matsjeh, S., Wahyuningsih, T.D., and Mustofa, 2012, Proceeding of 1st International Pharmacy Conference on Research and Practice, Universitas Islam Indonesia, Yogyakarta, 21-24 November 2012.

[14] Zangade, S., Mokle, S., Vibhute, A., and Vibhute, Y., 2011, Chem. Sci. J., 13, 1–6.

[15] Susanti, E.V.H., Matsjeh, S., Wahyuningsih, T.D., Mustofa, and Redjeki, T., 2014, Indo. J. Pharm., 25, 17–24.



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

Article Metrics

Abstract views : 2755 | views : 4406


Copyright (c) 2014 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 

Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web Analytics View The Statistics of Indones. J. Chem.