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Research on Chemical Intermediates

, Volume 38, Issue 1, pp 207–213 | Cite as

One-pot preparation of phenylpropanoid esters co-catalyzed by boric acid and piperidine

  • Huan Wang
  • Qing-Yi Wei
  • Hong Jiang
  • Zhen-Hua Jiang
Article
  • 300 Downloads

Abstract

Phenylpropanoid esters, especially those with hydroxyl and/or methoxy groups on the benzene ring, are important medicinal chemicals or intermediates. They are usually prepared by esterification of their corresponding substituted cinnamic acids with various alcohols. However, the esterification procedures often suffer from environmentally hazardous problems when sulfuric acid is used as a catalyst or suffer from unsatisfactory yields and expensive raw material when enzyme is applied as a catalyst. In this paper, a convenient one-pot process for preparing various phenylpropanoid esters from substituted benzaldehydes bearing hydroxyl and/or methoxyl groups has been developed. The alcohols react first with malonic acid catalyzed by boric acid to form monomalonate, then without separation, let the resultant mixture immediately react with the injected various substituted benzaldehydes in the presence of piperidine to afford the desired esters with moderate to good yields.

Keywords

One-pot Boric acid Phenylpropanoid esters Cinnamic acid 

Notes

Acknowledgments

This study was supported by the National Natural Science Foundation of China (Grant no. 20702016).

Supplementary material

11164_2011_338_MOESM1_ESM.doc (5.5 mb)
Supplementary material 1 (DOC 5650 kb)

References

  1. 1.
    J.D. Baranowski, C.W. Nagel, J. Food Sci. 47, 1587 (1982)CrossRefGoogle Scholar
  2. 2.
    A.T. Dinkova-Kostova, C. Abeygunawardana, P. Talalay, J. Med. Chem. 41, 5287 (1998)CrossRefGoogle Scholar
  3. 3.
    D. Grunberger, R. Banerjee, K. Eisinger, Experientia 44, 230 (1988)CrossRefGoogle Scholar
  4. 4.
    J. Bhattacharya, D.K. Chaudhuri, BBA-Gen. Subjects 343, 211 (1974)CrossRefGoogle Scholar
  5. 5.
    S.K. Gupta, A.B. Banerjee, B. Achari, Lloydia 39, 218 (1976)Google Scholar
  6. 6.
    J.D. Baranowski, C.W. Nagel, Appl. Environ. Microb. 45, 218 (1983)Google Scholar
  7. 7.
    A.H. Katz, C.A. Demerson, L.G. Humber, US 838,510 (11 March 1986)Google Scholar
  8. 8.
    H. Kikuzaki, M. Hisamoto, K. Hirose, J. Agric. Food Chem. 50, 2161 (2002)CrossRefGoogle Scholar
  9. 9.
    A. Neudörffer, D. Bonnefont-Rousselot, A. Legrand, J. Agric. Food Chem. 52, 2084 (2004)CrossRefGoogle Scholar
  10. 10.
    H.G. Chen, J.M. Tustin, P.G. Wuts, T.K. Sawyer, C.W. Smith, Int. J. Peptide Protein Res. 45, 1 (1995)CrossRefGoogle Scholar
  11. 11.
    S. Pattanaargson, N. Hongchinnagorn, P. Hirunsupachot, Photochem. Photobiol. 80, 322 (2004)CrossRefGoogle Scholar
  12. 12.
    A. Sinha, A. Sharma, A. Swaroop, V. Kumar, Tetrahedron 63, 1000 (2007)CrossRefGoogle Scholar
  13. 13.
    A.K. Chakraborti, B. Singh, S.V. Chankeshwara, J. Org. Chem. 74, 5967 (2009)CrossRefGoogle Scholar
  14. 14.
    S. Palaniappan, M. Sairam, J. Appl. Polym. Sci. 96, 1584 (2005)CrossRefGoogle Scholar
  15. 15.
    B.D. Hosangadi, R.H. Dave, Tetrahedron Lett. 37, 6375 (1996)CrossRefGoogle Scholar
  16. 16.
    B. Neises, Angew. Chem. Int. Edit. 17, 473 (1978)CrossRefGoogle Scholar
  17. 17.
    B. Guyot, B. Bosquette, M. Pina, Biol. Letters 19, 529 (1997)Google Scholar
  18. 18.
    R.T. Otto, H. Scheib, U.T. Bornscheuer, J. Mol. Catal. B-Enzym. 8, 201 (2000)CrossRefGoogle Scholar
  19. 19.
    J. Cassani, H. Luna, A. Navarro, Electron. J. Biotechn. 10, 508 (2007)Google Scholar
  20. 20.
    D.W. Brooks, N.C. Lee, R. Peevey, Tetrahedron Lett. 25, 4623 (1984)CrossRefGoogle Scholar
  21. 21.
    S.M. Levonis, L.F. Bornaghi, T.A. Houston, Aust. J. Chem. 60, 821 (2007)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  • Huan Wang
    • 1
  • Qing-Yi Wei
    • 1
  • Hong Jiang
    • 1
  • Zhen-Hua Jiang
    • 1
  1. 1.Department of ChemistryHuazhong Agricultural UniversityWuhanChina

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