Skip to main content
Log in

A mild, clean, and simple synthesis of symmetrical carboxylic anhydrides from carboxylic acides using a polymer supported tosyl chloride

  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

The use of polymeric reagents simplifies routine acylation of carboxylic acid because it eliminates the traditional purification. We describe the use of readily available cross-linked poly(4-vinylpyridine) supported tosyl chloride, [P4VP].TsCl, in the suspended solution phase synthesis of symmetrical anhydrides from carboxylic acids in the presence of K2CO3 in high yields and purity. The products can be obtained by filtration and evaporation of the solvent.

This is a preview of subscription content, log in via an institution to check access.

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. D.S. Tarbel, Account Chem. Res. 2 (1969) 296.

    Google Scholar 

  2. J. Meienhofer, in: E. Gross, J. Meienhofer (Eds.), The Peptides, Analysis, Synthesis and Biology, Vol. 1, Academic Press, New York, 1979, Chap. 6, p. 264.

    Google Scholar 

  3. M.A. Ogliarous, J.F. Wolfe, Synthesis of Carboxylic Acid, Esters and Their Derivatives, Wiley, New York, 1991, pp. 198–218.

    Book  Google Scholar 

  4. W.K. Fife, Z. Zahang, Tetrahedron Lett. 27 (1986) 4937.

    CAS  Google Scholar 

  5. P. Rambacher, S. Make, Angew. Chem. Intl. Ed. Engl. 7 (1968) 465 Angew. Chem. 80 (1968) 486.

    CAS  Google Scholar 

  6. S.R. Sandler, W. Karo, Organic Functional Group Preparation, Vol. 2, Academi Press, New York, 1972.

    Google Scholar 

  7. J.M. Adduci, R.S. Ramirez, Org. Prep. Proced. Int. 2 (1970) 321.

    CAS  Google Scholar 

  8. F. Chen, N.L. Benoiton, Synthesis (1970) 710.

    Google Scholar 

  9. Y. Kita, S. Akia, N. Ajimura, M. Yoahigi, T. Tsugoshi, H. Yasuda, Y. Tamura, J. Org. Chem. 51 (1986) 4150; and references cited therein.

    CAS  Google Scholar 

  10. K. Remigiusz, R. Juliatiek, M. Shahriar, J. Org. Chem. 59 (1994) 2913.

    Google Scholar 

  11. K.S. Keshavamurthy, Y.D. Vankar, D.N. Dhar, Synthesis (1982) 506.

    Google Scholar 

  12. S.G. Burton, P.T. Kaye, Synth. Commun. 19 (1989) 3331.

    CAS  Google Scholar 

  13. H. Adkinds, P.E. Thompson, J. Am. Chem. Soc. 71 (1949) 2242.

    Google Scholar 

  14. E.C. Tayo, G.W. Mclay, A. Mckillop, J. Am. Chem. Sos. 90 (1968) 2422.

    Google Scholar 

  15. Y. Hu, J.X. Wany, S. Li, Synth. Commun. 27 (1997) 243.

    CAS  Google Scholar 

  16. D. Plusqellec, F. Roulleau, M. Lefeuvre, E. Brown, E.C. Tayo, G.W. Mclay, A. Mckillop, J. Am. Chem. Sos. 90 (1968) 2422. Tetrahedron Let. 44 (1988) 2471.

    Google Scholar 

  17. F. Roulleau, D. Plusqellec, E. Brown, Tetrahedron Let. 24 (1983) 4195.

    CAS  Google Scholar 

  18. J.M. Wallace, J.E. Copenhaver, J. Am. Chem Soc. 63 (1941) 699.

    CAS  Google Scholar 

  19. D.H. Rammer, H.G. Khorana, J. Am. Chem. Soc. 85 (1963) 1997.

    Google Scholar 

  20. G.P. Liesen, C.N. Sukenik, J. Org. Chem. 52 (1987) 455.

    CAS  Google Scholar 

  21. J. Kim, D.O. Jang, Synth. Commun. 31 (2001) 395.

    CAS  Google Scholar 

  22. J. Kim, Y. Park, W.S. Lee, S. Cho, Y. Yoon, Synthesis (2003) 1517; and references cited Therein.

    Google Scholar 

  23. D.C. Sherrington, P. Hodge, In Synthesis and Separation Using Functional Polymers, John Wiley & Sons, 1988

    Google Scholar 

  24. D.C. Sherrington, P. Hodge, In Polymer-Supported Reactions in organic Synthesis, John Wiley & Sons, 1980

    Google Scholar 

  25. K. Tkemoto, Y. Inaki, R.M. Ottenbrite, In Functional Monomers and Polymers, Marcel Dekker Inc., New York, 1987.

    Google Scholar 

  26. A. Akelah, D.C. Sherington, Chem. Rew. 8 (1981) 577

    Google Scholar 

  27. A. Akelah, D.C. Sherington, Polymer 2 (1984) 1369.

    Google Scholar 

  28. S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Longbottom, M. Nesi, J.S. Scott, R.I. Storer, S.J. Taylor, J. Chem. Soc. Perkin Trans 1 (2000) 3815.

    Google Scholar 

  29. B. Tamami, N. Iranpoor, M.A. Karimi Zarchi, Polymer 34 (1993) 2011.

    CAS  Google Scholar 

  30. B. Tamami. M.A. Karimi Zarchi, Eur. Polym. J. 31 (1995) 715.

    CAS  Google Scholar 

  31. M.A. Karimi Zarchi, A. Zarei, J. Chin. Chem. Soc. 52 (2005) 309.

    Google Scholar 

  32. M.A. Karimi Zarchi, J. Noei, J. Appl. Polym. Sci. 104 (2007) 1064.

    Google Scholar 

  33. M.A. Karimi Zarchi, J. Chin. Chem. Soc. 54 (2007) 1299.

    Google Scholar 

  34. M.A. Karimi Zarchi, B.B.F. Mirjalili, N. Ebrahimi, Bull. Korean. Chem Soc. 29 (2008) 1079.

    Google Scholar 

  35. J.G. Rodrigues, R.M. Villamil, S. Ramos, New J. Chem. (1998) 865.

    Google Scholar 

  36. B. Tamami, A.R. Kiasat, J. Chem. Res. (1999) 444.

    Google Scholar 

  37. F. Hiashi, J. Nishi, J. Polym. Sci. A (1986) 701.

    Google Scholar 

  38. F. Kazemi, A.R. Kiasat, Phosphorous, Sulfur and Silicon 178 (2003) 2287.

    CAS  Google Scholar 

  39. M.S. Newman, P.K. Sujeeth, J. Org. Chem. (1978) 4367.

    Google Scholar 

  40. F. Kazemi, H. Sharghi, M.A. Naseri, Synthesis (2004) 205.

    Google Scholar 

  41. R.A. Fersht, W.P. Jencks, J. Am. Chem. Soc. 92 (1970) 5432.

    CAS  Google Scholar 

  42. J. Buckingham, S.M. Donaghy. Dictionary of Organic Compounds, 5th ed., Chapman and Hall, New York, 1982.

    Google Scholar 

  43. Z.J. Kaminski, B. Kolesinska, M. Malgorzata. Synthetic Commun. 34 (2004) 3349

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. A. Karimi Zarchi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Karimi Zarchi, M.A., Mirjalili, B.F., Kahrizsangi, Z.S. et al. A mild, clean, and simple synthesis of symmetrical carboxylic anhydrides from carboxylic acides using a polymer supported tosyl chloride. JICS 7, 455–460 (2010). https://doi.org/10.1007/BF03246032

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03246032

Keywords

Navigation