Issue

Vol. 36 No. 5 (2024): Vol 36 Issue 5, 2024

Copyright (c) 2024 Baramee Phungpis

Creative Commons License

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

Microwave Assisted Benzoin Condensation using N,N-Dimethylbenzimidazolium Iodide as an Efficient Greener Catalyst in Neutral Ionic Liquid [Bmim]BF4

https://doi.org/10.14233/ajchem.2024.31496
Baramee Phungpis
Faculty of Natural Resources, Rajamangala University of Technology Isan Sakonnakhon Campus, Sakon Nakhon 47160, Thailand
https://orcid.org/0000-0003-0202-8528
Pakin Noppawan
Department of Chemistry, Faculty of Science, Mahasarakham University, Maha Sarakham 44150, Thailand
https://orcid.org/0000-0002-6940-9045
Kanokkan Worawut
Faculty of Natural Resources, Rajamangala University of Technology Isan Sakonnakhon Campus, Sakon Nakhon 47160, Thailand
https://orcid.org/0000-0002-2485-4612

Corresponding Author(s) : Baramee Phungpis

barameephungpis@yahoo.com

Asian Journal of Chemistry, Vol. 36 No. 5 (2024): Vol 36 Issue 5, 2024

Abstract

The utilization of N,N-dimethylbenzimidazolium iodide as a catalyst in [Bmim]BF4 for benzoin condensation under microwave irradiation demonstrates its efficiency and eco-friendliness. This method enables the synthesis of α-hydroxy carbonyl compounds from various aromatic and heteroaromatic aldehydes with significant yields, ranging from good to high (89-96%). The reactions proceed swiftly, yielding no detectable byproducts. Moreover, the recycled reaction media, comprising benzimidazolium salt and NaOH after extraction, can be reused multiple times without a significant loss of efficiency.

Keywords

Benzoin [Bmin]BF4 N,N-Dimethylbenzimidazolium iodide Hydroxy carbonyl Microwave irradiation
Phungpis, B., Noppawan, P., & Worawut, K. (2024). Microwave Assisted Benzoin Condensation using N,N-Dimethylbenzimidazolium Iodide as an Efficient Greener Catalyst in Neutral Ionic Liquid [Bmim]BF4. Asian Journal of Chemistry, 36(5), 1191–1198. https://doi.org/10.14233/ajchem.2024.31496
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. J. Virkutyte and R.S. Varma, Chem. Sci., 2, 837 (2011); https://doi.org/10.1039/C0SC00338G
  2. M.N. Nadagouda, T.F. Speth and R.S. Varma, Acc. Chem. Res., 44, 469 (2011); https://doi.org/10.1021/ar1001457
  3. J. Kou and R.S. Varma, ChemSusChem, 5, 2435 (2012); https://doi.org/10.1002/cssc.201200477
  4. B. Baruwati and R.S. Varma, ChemSusChem, 2, 1041 (2009); https://doi.org/10.1002/cssc.200900220
  5. B. Baruwati, V. Polshettiwar and R.S. Varma, Green Chem., 11, 926 (2009); https://doi.org/10.1039/b902184a
  6. P. Schexnailder and G. Schmidt, Colloid Polym. Sci., 287, 1 (2009); https://doi.org/10.1007/s00396-008-1949-0
  7. V. Polshettiwar, M.N. Nadagouda and R.S. Varma, Aust. J. Chem., 62, 16 (2009); https://doi.org/10.1071/CH08404
  8. S. Connon, K. Zeitler, C. Rose and S. Gundala, Synthesis, 190 (2010); https://doi.org/10.1055/s-0030-1258363
  9. L.C. Lee, J.Y. Park, S.Y. Yoon, Y.H. Bae and S.J. Lee, Tetrahedron Lett., 45, 191 (2004); https://doi.org/10.1016/j.tetlet.2003.10.133
  10. R.E. Lutz and R.S. Murphey, J. Am. Chem. Soc., 71, 478 (1949); https://doi.org/10.1021/ja01170a030
  11. N.A. Meanwell, M.J. Rosenfeld, A.K. Trehan, J.L. Romine, J.J.K. Wright, C.L. Brassard, J.O. Buchanan, M.E. Federici, J.S. Fleming, M. Gamberdella, G. Zavoico and S.M. Seiler, J. Med. Chem., 35, 3498 (1992); https://doi.org/10.1021/jm00097a007
  12. P.A. Procopiou, C.D. Draper, J.L. Hutson, G.G. Inglis, B.C. Ross and N.S. Watson, J. Med. Chem., 36, 3658 (1993); https://doi.org/10.1021/jm00075a021
  13. V. Hahnvajanawong, W. Waengdongbung, S. Piekkaew, B. Phungpis and P. Theramongkol, Sci. Asia, 39, 50 (2013); https://doi.org/10.2306/scienceasia1513-1874.2013.39.050
  14. B. Phungpis, V. Hahnvajanawong and P. Theramongkol, Orient. J. Chem., 30, 933 (2014); https://doi.org/10.13005/ojc/300303
  15. B. Phungpis and K. Worawut, ASEAN J. Sci. Technol. Dev, 25, 1 (2022); https://doi.org/10.55164/ajstr.v25i1.245292
  16. V. Hahnvajanawong, W. Waengdongbung and P. Theramongkol, Orient. J. Chem., 32, 127 (2016); https://doi.org/10.13005/ojc/320113
  17. C.J. Pouchert, The Aldrich Library of NMR Spectra, Aldrich Chemical Co. (1983).
  18. A.S. Demir, Ö. Sesenoglu, E. Eren, B. Hosrik, M. Pohl, E. Janzen, D. Kolter, R. Feldmann, P. Dünkelmann and M. Müller, Adv. Synth. Catal., 344, 96 (2002); https://doi.org/10.1002/1615-4169(200201)344:1<96::AID-ADSC96>3.0.CO;2-Z
  19. E.J. Corey and F.Y. Zhang, Org. Lett., 1, 1287 (1999); https://doi.org/10.1021/ol990964z
  20. X. Ren and H. Du, J. Am. Chem. Soc., 138, 810 (2016); https://doi.org/10.1021/jacs.5b13104
  21. Z.Q. Rong, H.J. Pan, H.L. Yan and Y. Zhao, Org. Lett., 16, 208 (2014); https://doi.org/10.1021/ol4032045
  22. R. Breslow, J. Am. Chem. Soc., 80, 3719 (1958); https://doi.org/10.1021/ja01547a064
  23. J. Yan, R. Sun, K. Shi, K. Li, L. Yang and G. Zhong, J. Org. Chem., 83, 7547 (2018); https://doi.org/10.1021/acs.joc.8b00481
  24. Y. Liu, H. Wang, Y. Fu, Y. Qi and K. Yang, Synth. Commun., 44, 259 (2014); https://doi.org/10.1080/00397911.2013.804572
  25. T. Hischer, D. Gocke, M. Fernández, A.R. Alcántara, J. Sinisterra, P. Hoyos, W. Hartmeier and M.B. Ansorge-Schumacher, Tetrahedron, 61, 7378 (2005); https://doi.org/10.1016/j.tet.2005.05.082
  26. J. Buckingham, Dictionary of Organic Compounds, Chapman and Hall (1982).
  27. B. Phungpis and V. Hahnvajanawong, Asian J. Chem., 32, 2028 (2020); https://doi.org/10.14233/ajchem.2020.22711
  28. A. Miyashita, H. Matsuda, C. Iijima and T. Higashino, Chem. Pharm. Bull. (Tokyo), 38, 1147 (1990); https://doi.org/10.1248/cpb.38.1147
Read More
Author biographies is not available.
Statistic
Read Counter : 0 Download : 0