Skip to main content

Rapid oxidation of alcohols to aldehydes and ketones with chromium trioxide catalyzed by kieselguhr under solvent-free conditions

Research on Chemical Intermediates volume 39, pages 1015–1020 (2013)Cite this article

Abstract

A rapid and selective oxidation of alcohols to aldehydes and ketones with chromium trioxide catalyzed by kieselguhr under solvent-free conditions in yields between 90 and 98 % is described. The role of kieselguhr in this oxidation is not only as support but also as catalyst, even though the catalytic nature of the kieselguhr is currently unclear. The present oxidation is even faster than (or the same as) those assisted with microwave irradiations. Meanwhile, the influence of the water presence during the preparation of the reagent is considered.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Scheme 1

References

  1. L.F. Fieser, M. Fieser, Reagents for Organic Synthesis, vol. 1. (Wiley, New York, 1967), pp. 144–147, and subsequent volumes in the series

  2. F. Freeman, in Organic Synthesis by Oxidation with Metal Compounds, ed. by W.J. Mijs, C.R.H.I. de Jonge. (Plenum Press, New York, 1986), pp. 68–81

  3. A.H. Haines, Methods for the Oxidation of Organic Compounds, Alcohols, Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes and Aminoarenes (Academic, London, 1988), pp. 17–41

    Google Scholar 

  4. S.V. Ley, A. Madin, in Comprehensive Organic Synthesis, vol. 7, ed. by B.M. Trost, I. Fleming (Pergamon, London, 1991), pp. 251–289

    Chapter  Google Scholar 

  5. G. Cainelli, G. Cardillo, Chromium Oxidations in Organic Chemistry (Springer, Berlin, 1984)

    Book  Google Scholar 

  6. A. Mckillop, D.W. Young, Synthesis 401 (Part 1) and 481 (Part 2) (1979)

  7. P. Laszlo, Preparative Chemistry Using Supported Reagents (Academic, San Diego, 1987)

    Google Scholar 

  8. R.S. Varma, R.K. Saini, Tetrahedron Lett. 39, 1481 (1998), and references cited therein

  9. A.R. Kiasat, F. Kazemi, K. Nourbakhsh, Nourbakhsh Phosphorus Sulfur Silicon 179, 457 (2004)

    Article  CAS  Google Scholar 

  10. M.M. Heravi, N. Farhangi, Y.S. Beheshtiha, K. Assadolah, M. Ghassemzadeh, K. Tabar-hydar, Phosphorus Sulfur Silicon 177, 2883 (2002)

    Article  CAS  Google Scholar 

  11. M.M. Heravi, D. Ajami, K. Tabar-Hydar, M.J. Ghassemzadeh, Chem. Res. 334 (1999)

  12. R.S. Varma, Green Chem. 43 (1999)

  13. J.D. Lou, Synth. Commun. 19, 1841 (1989)

    Article  CAS  Google Scholar 

  14. J.D. Lou, W. Lou, Synth. Commun. 27, 3697 (1997)

    Article  CAS  Google Scholar 

  15. J.D. Lou, M. Wang, L. Zhu, Z. Fang, Catal. Commun. 4, 647 (2003)

    Article  CAS  Google Scholar 

  16. J.D. Lou, X. Chen, M. Wang, Oxid. Commun. 27, 610 (2004)

    CAS  Google Scholar 

  17. J.D. Lou, Y. Ma, C. Gao, L. Li, Synth. React. Inorg. Metal Org. Nano-Metal Chem. 36, 381 (2006)

    Article  CAS  Google Scholar 

  18. J.D. Lou, L. Zhu, Y. Ma, L. Li, Synth. Commun. 36, 3061 (2006)

    Article  CAS  Google Scholar 

  19. J.D. Lou, L. Li, N. Vatanian, X. Lu, X. Yu, Synth. React. Inorg. Metal Org. Nano-Metal Chem. 38, 373 (2008)

    CAS  Google Scholar 

  20. G.Q. Wang, C. Zhang, N. Vatanian, J.D. Lou, Synth. React. Inorg. Metal Org. Nano-Metal Chem. 38, 481 (2008)

    CAS  Google Scholar 

  21. J.D. Lou, C. Zhang, G. Wang, C. Gao, Synth. React. Inorg. Metal Org. Nano-Metal Chem. 39, 6 (2009)

    CAS  Google Scholar 

  22. L. Huang, Q. Wang, Y. Ma, J.D. Lou, C. Zhang, Synth. Commun. 41, 1682 (2011)

    Article  CAS  Google Scholar 

  23. J.D. Lou, J. Ge, X.N. Zou, C. Zhang, Q. Wang, Y.C. Ma, Oxid. Commun. 34, 361 (2011)

    CAS  Google Scholar 

  24. J.D. Lou, X. Lu, L. Huang, C. Zhang, Q. Wang, X. Zou, Synth. React. Inorg. Metal Org. Nano-Metal Chem. 41, 1278 (2011)

    Article  CAS  Google Scholar 

  25. L. Huang, J.D. Lou, Y. Ma, Q. Wang, C. Zhang, Adsorpt. Sci. Technol. 29, 871 (2011)

    Article  CAS  Google Scholar 

  26. J.D. Lou, F. Lin, X. Lu, Q. Wang, X. Zou, Synth. React. Inorg. Metal Org. Nano-Metal Chem. 42, 282 (2012)

    Article  CAS  Google Scholar 

  27. W. Zheng, C. Huang, C. Zhang, Y.-F. Zhou, J.D. Lou, Res. Chem. Intermed. (2012). doi:10.1007/s11164-012-0573-2

  28. J.D. Lou, Z.N. Xu, Tetrahedron Lett. 43, 6095 (2002)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Life Sciences, China Jiliang University, Hangzhou, 310018, Zhejiang, China

    Ai He, Jie Zhang, Wenjin Zheng, Lihong Huang & Ji-Dong Lou

  2. China Pharmaceutical University, Nanjing, 210009, Jiangsu, China

    Chen Huang

  3. Centre for the Research and Technology of Agro-Environmental and Biological Sciences (CITAB)/Department of Biology and Environment, Universidade de Trás-os-Montes e Alto Douro (UTAD), Apartado 1013, 5001-801, Vila Real, Portugal

    Changhe Zhang

  4. Sirnaomics, Inc., 401 Professional Drive, Gaithersburg, MD, 20879, USA

    Ji-Dong Lou

Authors
  1. Ai He
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jie Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wenjin Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Chen Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Changhe Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Lihong Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ji-Dong Lou
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ji-Dong Lou.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

He, A., Zhang, J., Zheng, W. et al. Rapid oxidation of alcohols to aldehydes and ketones with chromium trioxide catalyzed by kieselguhr under solvent-free conditions. Res Chem Intermed 39, 1015–1020 (2013). https://doi.org/10.1007/s11164-012-0663-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0663-1

Keywords

  • Oxidation
  • Chromium trioxide
  • Kieselguhr
  • Catalysis