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Document Type : Original Article


1 Department of Chemistry, Osmania University, Telangana State, Hyderabad 500007, India

2 Department of Bio-Chemistry, Osmania University, Telangana State, Hyderabad 500007, India


In the present study, AgNO3 is employed as an effective catalyst for transesterification of β-keto esters with various alcohols under conventional and non-conventional conditions. The alcohols are easily converted into corresponding acetates in very good yields and less reaction times. However, a decrease in reaction times as well as moderate yields were observed when performed under non-conventional conditions such as Sonication and Microwave irradiation. Contrary to many other silver salts catalysts, AgNO3 has shown remarkable levels of activity and stability towards transesterification reaction. The tendency in reaction rates was found to be MWAS (3-6 min) <<< Sonication (30-45 min) <<< Conventional (8-12 hrs).

Graphical Abstract

Rate Accelerations in AgNO3 Mediated Transesterification of β –Keto esters


Main Subjects

  1. Wilhelm Riemenschneider and Hermann M. Bolt "Esters, Organic" Ullmann's Encyclopaedia of Industrial Chemistry, 2005
  2. (a) Yuzawa H., Tanaka K., Kariyane K. Tetrahedron Lett., 1974, 15:3995; (b) Blossey E.C., Turner L.M., Neckers D.C. Tetrahedron Lett, 1973, 14:1823
  3. (a) Taft R.W., Newman M.S., Verhoek F.H. J. Am. Chem. Soc, 1950, 72:4511; (b) Billman J.H., Smith W.T., Rendall J.L. J. Am. Chem. Soc, 1947, 69:2058; (c) Osipow L., Snell F.D., York W.C., Finchler A., Ind. Eng. Chem, 1956, 48:1459; (d) Osipow L., Snell F.D., Finchler A. J. Am. Oil Chem. Soc, 1957, 34:185 (e) Komori S., Okahara M., Okamoto K. J. Am. Oil Chem. Soc, 1960, 37:468; (f) Gilbert J.C., Kelly T.A. J. Org. Chem, 1988, 53:449; (g) Seebach D., Thaler A., Blaser D., Ko S.Y., HelvChimActa, 1991, 74:1102
  4. Cordova A., Janda K.D. J. Org. Chem, 2001, 66:1906
  5. (a) Rehberg C.E., Fisher C.H. J. Am. Chem. Soc, 1944, 66:1203; (b) Rehberg C.E., Faucette W.A., Fisher C.H. J. Am. Chem. Soc, 1944, 66:1723; (c) Rehberg C.E. Organic Synthesis; Wiley: New York, 1955, 3:146; (d) Haken J.K. J. Appl. Chem, 1963, 13:168
  6. (a) Otera J."Transesterification". Chemical Reviews. 1993, 93l1449
  7. Claisen L., Claparede A. Ber. Deut. Chem. Ges, 1881, 14:2460
  8. Yang J., Ji C., Zhao Y., Li Y., Jiang S., Zhang Z., Ji Y., Liu W. Synth Comm, 2010, 40:957
  9. Emmer G. Tetrahedron, 1992, 48:7165
  10. Magriotis P.A., Johnson F. J. Org. Chem,1984, 49:1460
  11. Benbakkar M., Baltas M., Gorrichon L., Gorrishon J.P.  Synth. Comm, 1989, 9:3241
  12. Chavan S.P., Pasupathy K., Shengule S., Shinde V., Anand R. ARKIVOC,  2005, xiii:162
  13. Chavan S.P., Rao T.S., Dantale S.W., Sivappa R. Synth. Comm, 2001, 32:289
  14. (a) Chavan S.P., Shivasankar K., Sivappa R., Kale R.R. Tetrahedron Lett, 2002, 43:8583; (b) Bo W., Ming Y.L., Shuan S.J. Tetrahedron Lett, 2003, 44:5037
  15. (a) Balaji B.S., Sasidharan M., Kumar R., Chanda B. Chem. Comm,1996, 1996:707; (b) Balaji B.S., Chanda B.M. Tetrahedron, 1998, 54:13237; (c) Ponde D., Deshpande V.H., Bulbule V.J., Sudalai A., Gajare A.S. J. Org. Chem, 1998, 63:1058 ; (d) Kumar P., Pandey R.K. Synlett, 2000, 2000:251; (e) Christopher’s J.,  Onal N. Eur. J. Org. Chem, 2000, 2000:1633
  16. Magens S., Plietker B. J. Org. Chem, 2010, 75:3715
  17. Weng S.S., Ke C.S., Chen F.K., Lyu Y.F., Lin G.Y. Tetrahedron, 2011, 67:1640
  18. Gui J., Cong X., Liu D., Zhang X., Hu Z., Sun Z. CatalComm, 2004, 5:473
  19. Li X., Eli W., Li G., CatalComm, 2008, 9:2264
  20. Ren Y.  Synth. Comm, 2010, 40:1670
  21. Otera J. Acc. Chem. Res, 2004, 37:288
  22. Das R., Chakraborty D. Synthesis, 2011, 10:1621
  23. Chakraborty D., Gowda R.R., Malik P. Tetrahedron Lett, 2009, 50:6553
  24. Das R., Chakraborty D. Synthesis, 2011, 2:277
  25. (a) Suslick K.S. Ultrasound: It’s Chemical, Physical and Biological Effects; VCH: New York, 1988; (b) Mason T.J. Chemistry with Ultrasound; Elsevier Science Publishers: London, 1990
  26. (a) Singh V., Kaur K.P., Khurana A., Kad G.L. Resonance, 1998, 3:56; (b) Mason T.J., Peters D. Practical Sonochemistry: Power Ultrasound Uses and Applications, 2nd Ed.; Harwood Publishing: Chichester, 2003
  27. Nüchter M., Ondruschka B., Bonrath W., Gum A., Green chemistry, 2004, 2004:128