Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Efficient Protection of Alcohols with Carboxylic Acids Using a Variety of Heteropolyoxometallates as Catalysts, Studying Effective Reaction Parameters

  • Tayebee, Reza (Department of Chemistry, Sabzevar Tarbiat Moallem University) ;
  • Cheravi, Fatemeh (Department of Chemistry, Sabzevar Tarbiat Moallem University)
  • Published : 2009.12.20
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Abstract

Esterification is an important class of reactions in the preparation of perfumery and flavor chemicals, wherein homogeneous, solid acidic, and superacidic catalysts are normally used. Now, an efficient and selective protocol for protection of various functionalized alcohols employing carboxylic acids as protecting agents is realized through the catalytic mediation of simple heteropolyoxometallates. In this methodology, water is the only by-product and notably the aspect of effluent treatments does not arise. The advantages include the operational simplicity, recycle ability of the catalyst and mild reaction conditions. The present catalytic system may be a potential candidate not only for laboratory practice but also for commercial applications and offers an environmentally safer alternative to the existing processes.

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References

  1. Cope, A. C.; Herrick, E. C. Org. Synth. 1963, 4, 304
  2. Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, 61, 4560 https://doi.org/10.1021/jo952237x
  3. Procopiou, P. A.; Baugh, S. P. D.; Flank, S. S.; Inglis, G. A. Chem. Commun. 1996, 2625 https://doi.org/10.1039/cc9960002625
  4. Baker, R. H.; Bordwell, F. G. Org. Synth. Coll. 1955, 3, 141
  5. Iqbal, J.; Srivastva, R. R. J. Org. Chem. 1992, 57, 2001 https://doi.org/10.1021/jo00033a020
  6. Sarel, S.; Newman, M. S. J. Am. Chem. Soc. 1956, 78, 5416 https://doi.org/10.1021/ja01601a068
  7. Hossain, N.; Magnussan, G. Tetrahedron Lett.1999, 40, 2217 https://doi.org/10.1016/S0040-4039(99)00175-6
  8. Matute, B. M.; Backvall, J.-E. J. Org. Chem. 2004, 69, 9191 https://doi.org/10.1021/jo048511h
  9. Orita, A.; Ito, T.; Yasui, Y.; Otera, J. Syn. Lett. 1999, 1927
  10. Adam, W.; Moller, C. R. S.; Schmid, K. S. J. Org. Chem. 2001, 66, 7365, and references therein https://doi.org/10.1021/jo010549w
  11. Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171 https://doi.org/10.1021/cr960400y
  12. Okuhara, T.; Mizuno, N.; Misono, M. Adv. Catal. 1996, 41, 113 https://doi.org/10.1016/S0360-0564(08)60041-3
  13. Jansen, R. J. J.; van Veldhuizen, H. M.; Schwegler, M. A.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas. 1994, 113, 115 https://doi.org/10.1002/recl.19941130302
  14. Misono, M.; Nojiri, N. Appl. Catal. 1990, 64, 1 https://doi.org/10.1016/S0166-9834(00)81550-X
  15. Tiofeeva, M. N.; Dimidov, A. V.; Kozhevnikov, I. V. J. Mol. Catal. 1979, 179, 21
  16. Drago, R. S.; Dias, J. A.; Maier, T. J. Am. Chem. Soc. 1997, 119, 7702 https://doi.org/10.1021/ja9639123
  17. Alizadeh, M. H.; Tayebee, R. J. Braz. Chem. Soc. 2005, 16, 108 https://doi.org/10.1590/S0103-50532005000100017
  18. Alizadeh, M. H.; Razavi, H.; Bamoharram, F. F. J. Mol. Catal. A: Chem. 2003, 200, 105 https://doi.org/10.1016/S1381-1169(03)00043-8
  19. Tayebee, R. J. Korean Chem. Soc. 2008, 52(1), 23 https://doi.org/10.5012/jkcs.2008.52.1.023
  20. Alizadeh, M. H.; Harmalker, S. P.; Jeanin, Y.; Pope, M. T. J. Am. Chem. Soc. 1985, 107, 2662 https://doi.org/10.1021/ja00295a019
  21. Alizadeh, M. H.; Kermani1, T.; Tayebee, R. Monatsh. Chem. 2007, 138, 165. https://doi.org/10.1007/s00706-006-0573-2
  22. Alizadeh, M. H.; Tayebee, R. Monatsh. Chem. 2006, 137, 1063 https://doi.org/10.1007/s00706-006-0507-z
  23. Tayebee, R.; Rafiee, E. Bull. Chem. Soc. Ethiop. 2006, 20(2), 1
  24. Tayebee, R.; Mahdavi, B. Asian Journal of Chemistry 2009, 21, 1565
  25. Tayebee, R.; Alizadeh, M. H. Cur. Sci. 2007, 93, 133
  26. Tayebee, R.; Alizadeh, M. H. Chin. J. Chem. 2007, 25, 1031 https://doi.org/10.1002/cjoc.200790165
  27. Tayebee, R.; Alizadeh, M. H. Monatsh. Chem. 2007, 138, 763 https://doi.org/10.1007/s00706-007-0660-z
  28. Green, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis, 3rd ed.; Wiley-Interscience, New York: 1999
  29. Altiokka, M. R.; Citak, A. Appl. Catal. A: Gen. 2003, 239, 141 https://doi.org/10.1016/S0926-860X(02)00381-2
  30. Chen, X.; Xu, Z.; Okuhara, T. Appl. Catal. A: Gen. 1999, 180, 261 https://doi.org/10.1016/S0926-860X(98)00337-8
  31. Liu, W. T.; Tan, C. S. Liquid-Phase Ind. Eng. Chem. Res. 2001, 40, 3281 https://doi.org/10.1021/ie001059h
  32. Yadav, G. D.; Thathagar, M. B.; React. Funct. Polym. 2002, 52, 99 https://doi.org/10.1016/S1381-5148(02)00086-X
  33. Hoek, I.; Nijhuis, T. A.; Stankiewicz, A. I.; Moulijn, J. A. Appl. Catal. A: Gen. 2004, 266, 109 https://doi.org/10.1016/j.apcata.2004.02.005
  34. Kirumakki, S. R.; Nagaraju, N.; Narayanan, S. Appl. Catal. A: Gen. 2004, 273, 1 https://doi.org/10.1016/j.apcata.2004.03.016
  35. Hiyoshi, M.; Lee, B.; Lu, D.; Hara, M.; Kondo, J. N.; Domen, K. Catal. Lett. 2004, 98, 181 https://doi.org/10.1007/s10562-004-8678-x
  36. Iizuka, T.; Fujie, S.; Ushikubo, T.; Chen, Z. H.; Tanabe, K. Appl. Catal. 1986, 28, 1 https://doi.org/10.1016/S0166-9834(00)82488-4
  37. Okun, N. M.; Anderson, T. M.; Hill, C. L. J. Am. Chem. Soc. 2003, 125, 3194 https://doi.org/10.1021/ja0267223
  38. ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 258, 1636 https://doi.org/10.1126/science.287.5458.1636
  39. ten Brink, G. J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355 https://doi.org/10.1002/1615-4169(200206)344:3/4<355::AID-ADSC355>3.0.CO;2-S
  40. North, E. O. Inorg. Synth. 1993, 1, 129 https://doi.org/10.1002/9780470132326.ch48
  41. Wu, H. J. Biol. Chem. 1920, 43, 189
  42. Brevard, C.; Schimpf, R.; Tourne, G.; Tourne, C. M. J. Am. Chem. Soc. 1983, 105, 7059 https://doi.org/10.1021/ja00362a008
  43. CRC, Handbook of Tables for Organic Compound Identification, 3rd and 54th ed

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