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Synthesis of 1-{6-(2-methylbenzoyl)-N-ethylcarbazole-3-yl}-ethane-1-one oxime O-acetate

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Abstract

1-{6-(2-Methylbenzoyl)-N-ethylcarbazole-3-yl}-ethane-1-one oxime O-acetate, an excellent two-photon carbazole photoinitiator, was synthesized with moderate yield (76.9%) starting from the successive o-methyl benzoylation and acetylation of N-ethylcarbazole, followed by oximation and esterification in the article. The structure was confirmed by 1H-NMR, 13C-NMR, and IR. The by-product acetic acid in the neutralization of hydroxylamine hydrochloride is effectively utilized in esterification with the aid of the one-pot process. In particular, the phase transfer technique is applied to overcome the deficiency of low reaction rate caused by heterogeneous reaction conditions in esterification.

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References

  1. K. Dietliker, T. Jung, J. Benkhoff, H. Kura, A. Matsumoto, H. Oka, D. Hristova, G. Gescheidt, G. Rist, Macromol. Symp. 217, 77 (2004)

    Article  CAS  Google Scholar 

  2. C. Decker, Prog. Polym. Sci. 21, 593 (1996)

    Article  CAS  Google Scholar 

  3. E. Beck, E. Keil, M. Lokai, J. Schroder, K. Sass, Mod. Paint Coat. 88, 36 (1998)

    CAS  Google Scholar 

  4. L.N. Price, J. Coat. Technol. 67, 27 (1995)

    CAS  Google Scholar 

  5. Y. Qian, W. Huang, Z.F. Lu, K. Meng, C.G. Lu, Y.P. Cui, J. Southeast Univ. 24, 234 (2008)

    CAS  Google Scholar 

  6. S. Maruo, O. Nakamura, S. Kawata, Opt. Lett. 22, 132 (1997)

    Article  CAS  Google Scholar 

  7. H.B. Sun, T. Kawakami, Y. Xu, J.Y. Ye, S. Matuso, H. Misawa, M. Miwa, R. Kaneko, Opt. Lett. 25, 1110 (2000)

    Article  CAS  Google Scholar 

  8. P. Galajda, P. Ormos, Appl. Phys. Lett. 80, 4653 (2002)

    Article  CAS  Google Scholar 

  9. K.J. Schafer, J.M. Hales, M. Balu, K.D. Belfield, E.W. Van Stryland, D.J. Hagan, J. Photochem. Photobiol. A. 162, 497 (2004)

    Article  CAS  Google Scholar 

  10. Y. Ren, X.Q. Yu, D.J. Zhang, D. Wang, M.L. Zhang, G.B. Xu, X. Zhao, Y.P. Tian, Z.X. Shao, M.H. Jiang, J. Mater. Chem. 12, 3431 (2002)

    Article  CAS  Google Scholar 

  11. B. Koenig, M. Pelka, H. Zieg, T. Ritter, H. Bouas-Laurent, H. Bonneau, J.P. Desvergne, J. Am. Chem. Soc. 121, 1681 (1999)

    Article  CAS  Google Scholar 

  12. T. Sasaki, H. Takakuwa, K. Shimada, U.S. Patent 20070099096, 3 May 2007

  13. L. Gong, C. Qing, X.Z. Chen, Res. Chem. Intermed. 36, 383 (2010)

    Article  CAS  Google Scholar 

  14. Q.R. Chen, Y. Feng, C. Xie, Chem. Res. Appl. 20, 603 (2008)

    CAS  Google Scholar 

  15. K. Kunimoto, J. Tanabe, H. Kura, H. Oka, M. Ohwa, WO Patent 02100903, 19 December 2002

Download references

Acknowledgments

We gratefully acknowledge the generous financial support by grants from the National Natural Science Foundation of China (No. 21076183, 21006087) and the Natural Science Foundation of the Zhejiang Province (No. Y4100147).

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Authors and Affiliations

  1. Department of Chemical and Biochemical Engineering, State Key Laboratory of Chemical Engineering, Zhejiang University, No.38 Zheda Road, Hangzhou, 310027, China

    Liang Zhao, Chao Qian, Ling Gong & Xin-zhi Chen

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  1. Liang Zhao
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  2. Chao Qian
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  3. Ling Gong
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  4. Xin-zhi Chen
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Correspondence to Chao Qian.

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Zhao, L., Qian, C., Gong, L. et al. Synthesis of 1-{6-(2-methylbenzoyl)-N-ethylcarbazole-3-yl}-ethane-1-one oxime O-acetate. Res Chem Intermed 38, 105–111 (2012). https://doi.org/10.1007/s11164-011-0329-4

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