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A highly efficient synthetic method for the preparation of 3,4-dimethylbenzaldehyde from o-xylene in aqueous media

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Abstract

In this study, 3,4-dimethylbenzaldehyde was obtained in 82.3% total yield by oxidation of 3,4-dimethylbenzyl chloride with NaNO3/AcOH catalyzed by PEG-600 in aqueous media. The starting material 3,4-dimethylbenzyl chloride was prepared by chloromethylation of o-xylene in CTAB micellar catalytic system. Compared with other synthetic methods, this method not only enhanced the yield, but also afforded an efficient work-up procedure. The structures of the products were confirmed by Elemental analysis, 1H NMR and 13C NMR or compared with authentic samples.

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References

  1. Y.C. Miao, D.W. Li, J.Z. Yang, China Plastics 14 (2000) 66.

    CAS  Google Scholar 

  2. K.Z. Wang, Plastic Additives, Chemical Industry Press, Beijing, 2003.

    Google Scholar 

  3. Y.C. Miao, China Plastics 14 (2000) 19–23.

    CAS  Google Scholar 

  4. Y.L. Wu, W.G. Wang, S.F. Chen, C.W. Wang, Guangdong Chemical Industry 12 (2006) 17.

    Google Scholar 

  5. Z.Y. Yin, Y.Y. Li, L. Guo, Chemical World 3 (2006) 174.

    Google Scholar 

  6. K.X. Xu, Processing of Fine Chemical Industrial Raw Materials and Intermediates, Chemical Industry Press, Beijing, 1998.

    Google Scholar 

  7. L. Gatterman, J.A. Koch, Chem. Ber. 30 (1897) 1622.

    Google Scholar 

  8. E.R. Gray, C.N. Masten, U.S. Patent 3284508, 1966.

  9. S. Fujiyama, T. Takahashi, S. Kozao, U.S. Patent 3948998, 1976.

  10. G.A. Olah, F. Pelizza, S. Kobayashi, J.A. Olah, J. Am. Chem. Soc. 98 (1976) 296.

    CAS  Google Scholar 

  11. S.H. Vanderpool, U.S. Patent 4218403, 1980.

  12. G.A. Olah, K. Laali, O. Farooq, J. Org. Chem. 50 (1985) 1483.

    CAS  Google Scholar 

  13. Toshiaki, Kobayashi, Nara, K. Kujitani, U.S. Patent 4902807, 1990.

  14. M. Tanaka, J. Iyoda, Y. Souma, J. Org. Chem. 57 (1992) 2677.

    CAS  Google Scholar 

  15. Saleh, Ramzi, Yanni, W.O. Patent 0015593A2, 2000.

  16. A.S. Walter, G.L. John, U.S. Patent 6087537, 2000.

  17. W. Partenheimer, Catal. Today 23 (1995) 69.

    CAS  Google Scholar 

  18. Y. Yoshino, Y. Hayashi, T. Iwahama, S. Sakaguchi, Y. Ishii, J. Org. Chem. 62 (1997) 6810.

    CAS  Google Scholar 

  19. C.T. Zhao, C.N. Patent 1439744, 2003.

  20. V.K. Balakrishnan, E. Buncel, G.W. Vanlood, Environ. Sci. Technol. 39 (2005) 5824.

    CAS  Google Scholar 

  21. T. Dwars, E. Paetzold, G. Oehme, Angew. Chem. Int. Ed. 44 (2005) 7174.

    CAS  Google Scholar 

  22. Q.F. Liu, M. Lu, Y.Q. Li, J. Mol. Catal. A: Chem. 277 (2007) 113.

    CAS  Google Scholar 

  23. C.M. Stark, C.L. Liotta, Phase Transfer Catalysis Principles and Techniques, Academic Press, New York, 1978.

    Google Scholar 

  24. E. Kaczmarczyk, E. Janus, E. Milchert, J. Mol. Catal. A: Chem. 244 (2006) 173.

    CAS  Google Scholar 

  25. S.L. Regen, A. Nigam, J.J. Besse, Tetrahedron Lett. 19 (1978) 2757.

    Google Scholar 

  26. A.R. Jones, Quaternary Ammonium Salts: Their Use in Phase Transfer Catalysis (Best Synthetic Methods), Elsevier, Amsterdam, 2001.

    Google Scholar 

  27. B.Y. Zhu, Z.G. Zhao, Fundamentals of Interfacial Chemistry, Chemical Industry Press, Beijing, 1996.

    Google Scholar 

  28. R.C. Fuson, C.H. McKeever, Organic Reactions, John Wiley, Vol. 1, New York, 1943, pp. 63–90.

    Google Scholar 

  29. G.A. Olah, Friedel Crafts and Related Reactions, Part 2, John Wiley, New York, 1964, Vol. 2, pp. 659–784.

    Google Scholar 

  30. K. Qiao, Y.Q. Deng, Acta Chim. Sin. 61 (2003) 133.

    CAS  Google Scholar 

  31. Y. Wang, Z.C. Shang, T.X. Wu, Synth. Commun. 36 (2006) 3053.

    CAS  Google Scholar 

  32. Y.X. Fang, Y.Q. Deng, Q.G. Ren, Chin. J. Chem. Eng. 16 (2008) 357.

    CAS  Google Scholar 

  33. T. Kishida, T. Yamauchi, Y. Kubota, Green Chem. 6 (2004) 57.

    CAS  Google Scholar 

  34. T. Nishimura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem. 64 (1999) 6750.

    CAS  Google Scholar 

  35. S. Chandrasekhar, M. Sridhar, Tetrahedron Lett. 41 (2000) 5423.

    CAS  Google Scholar 

  36. S. Das, A.K. Panigrahi, G.C. Maikap, Tetrahedron Lett. 44 (2003) 1375.

    CAS  Google Scholar 

  37. C. Li, P. Zheng, J. Li, H. Zhang, Y. Cui, Q. Shao, Angew. Chem. Int. Ed. 42 (2003) 5063.

    CAS  Google Scholar 

  38. J.N. Moorthy, N. Singhal, K. Senapati, Tetrahedron Lett. 47 (2006) 1757.

    CAS  Google Scholar 

  39. A. Itoh, T. Kodana, S. Inagaki, Y. Masaki, Org. Lett. 2 (2000) 2455.

    CAS  Google Scholar 

  40. M.M. Khodaei, A.R. Khosropour, M. Jowkar, Synthesis (2005) 1301.

    Google Scholar 

  41. H. Alinezhad, M. Tajbakhsh, R. Soleimani, J. Iran. Chem. Soc. 6 (2009) 288.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Chemical Engineering College, Nanjing University of Science and Technology, Nanjing, 210094, PR China

    Y. L. Hu, M. Lu, Q. F. Liu, W. Wei & X. Liu

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  1. Y. L. Hu
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  2. M. Lu
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  3. Q. F. Liu
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  4. W. Wei
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  5. X. Liu
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Correspondence to M. Lu.

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Hu, Y.L., Lu, M., Liu, Q.F. et al. A highly efficient synthetic method for the preparation of 3,4-dimethylbenzaldehyde from o-xylene in aqueous media. JICS 7, 487–494 (2010). https://doi.org/10.1007/BF03246036

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  • DOI: https://doi.org/10.1007/BF03246036

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