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An Efficient Approach for the Deprotection of Esters Using Ionic Liquid as Nucleophile
Corresponding Author(s) : Benmei Wei
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
An efficient approach for the deprotection of esters has been developed using ionic liquid as nucleophile in the presence of protic acid. Using methyl benzoate as a model compound, the best result was obtained by the combination of 1-methylimidazolium bromide and methane sulfonic acid with a conversion of 96 % after 2 h at 120 ºC.
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- E.M. Keramane, B. Boyer and J.P. Roque, Tetrahedron Lett., 42, 855 (2001).
- D.A. Evans, D.H.B. Halstead and D.P. Campos, J. Am. Soc. Chem., 121, 6816 (1999).
- A. Loupy, M. Pedoussaut and J. Sansoulet, J. Org. Chem., 51, 740 (1986).
- G. Blay, M.L. Cardona, M.B. Garcia and J.R. Pedro, Synthesis, 438 (1989).
- Y.Q. Wu, D.C. Limburg, D.E. Wilkinson, M.J. Vaal and G.S. Hamilton, Tetrahedron Lett., 41, 2847 (2000).
- R. Kaul, Y. Brouillette, Z. Sajjadi, K.A. Hansford and W.D. Lubell, J. Org. Chem., 69, 6131 (2004).
- P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed., 39, 3772 (2000).
- J.S. Wilkes, J. Mol. Catal. A, 214, 11 (2003).
- V.I. Parvulescu and C. Hardacre, Chem. Rev., 107, 2615 (2007).
- S. Zhou, L. Liu, B. Wang, F. Xu and R. Su, Asian J. Chem., 25, 240 (2013).
- X. Sun, H. Luo and S. Dai, Chem. Rev., 112, 2100 (2012).
- H. Sheikhloie, M.S. Tehrani and S.W. Husain, Asian J. Chem., 25, 1831 (2013).
- D. Ingildeev, F. Hermanutz, K. Bredereck and F. Effenberger, Macromol. Mater. Eng., 297, 585 (2012).
- Z. Jiao and X. Fang, Asian J. Chem., 25, 2143 (2013).
- H. Ohno, "Electrochemical Aspects of Ionic Liquids", Wiley, New York (2005).
- Q. Ren, S. Dong, J. Wu, F. Li and J. Miao, Asian J. Chem., 24, 5377 (2012).
- M.D. Joshi and J.L. Anderson, RSC Adv., 2, 5470 (2012).
- L. Wang, H. Zhu, C. Ma and Y. Yan, Asian J. Chem., 25, 2129 (2013).
- S. Boovanahalli, D.W. Kim and D. Chi, J. Org. Chem., 69, 3340 (2004).
- R. Sheldon, Chem. Commun., 2399 (2001).
- N. Gupta, G.L. Kad and J. Singh, Catal. Commun., 8, 1323 (2007).
- A.R. Hajipour, M. Mostafavi and A.E. Ruoho, Monatsh. Chem., 138, 569 (2007).
- B.M. Wei, Z.Y. Zhang, Z.Q. Dai and K.C. Zhang, Monatsh. Chem., 142, 1029 (2011).
- E. Janus, L. Goc-Maciejewska, M. Lozynski and J. Pernak, Tetrahedron Lett., 47, 4079 (2006).
- H. Guo, J.L. Wang, X. Li, D.S. Lv and X.F. Lin, Chin. J. Catal., 32, 162 (2011).
- B.J. Cox, S. Jia, Z.C. Zhang and J.G. Ekerdt, Polym. Degrad. Stab., 96, 426 (2011).
- J. Buckingham, Dictionary of Organic Compounds, Routledge, New York (1982).
- N.L. Lancaster, T. Weltib and G.B. Yong, J. Chem. Soc., Perkin Trans. II, 2267 (2001)
References
E.M. Keramane, B. Boyer and J.P. Roque, Tetrahedron Lett., 42, 855 (2001).
D.A. Evans, D.H.B. Halstead and D.P. Campos, J. Am. Soc. Chem., 121, 6816 (1999).
A. Loupy, M. Pedoussaut and J. Sansoulet, J. Org. Chem., 51, 740 (1986).
G. Blay, M.L. Cardona, M.B. Garcia and J.R. Pedro, Synthesis, 438 (1989).
Y.Q. Wu, D.C. Limburg, D.E. Wilkinson, M.J. Vaal and G.S. Hamilton, Tetrahedron Lett., 41, 2847 (2000).
R. Kaul, Y. Brouillette, Z. Sajjadi, K.A. Hansford and W.D. Lubell, J. Org. Chem., 69, 6131 (2004).
P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed., 39, 3772 (2000).
J.S. Wilkes, J. Mol. Catal. A, 214, 11 (2003).
V.I. Parvulescu and C. Hardacre, Chem. Rev., 107, 2615 (2007).
S. Zhou, L. Liu, B. Wang, F. Xu and R. Su, Asian J. Chem., 25, 240 (2013).
X. Sun, H. Luo and S. Dai, Chem. Rev., 112, 2100 (2012).
H. Sheikhloie, M.S. Tehrani and S.W. Husain, Asian J. Chem., 25, 1831 (2013).
D. Ingildeev, F. Hermanutz, K. Bredereck and F. Effenberger, Macromol. Mater. Eng., 297, 585 (2012).
Z. Jiao and X. Fang, Asian J. Chem., 25, 2143 (2013).
H. Ohno, "Electrochemical Aspects of Ionic Liquids", Wiley, New York (2005).
Q. Ren, S. Dong, J. Wu, F. Li and J. Miao, Asian J. Chem., 24, 5377 (2012).
M.D. Joshi and J.L. Anderson, RSC Adv., 2, 5470 (2012).
L. Wang, H. Zhu, C. Ma and Y. Yan, Asian J. Chem., 25, 2129 (2013).
S. Boovanahalli, D.W. Kim and D. Chi, J. Org. Chem., 69, 3340 (2004).
R. Sheldon, Chem. Commun., 2399 (2001).
N. Gupta, G.L. Kad and J. Singh, Catal. Commun., 8, 1323 (2007).
A.R. Hajipour, M. Mostafavi and A.E. Ruoho, Monatsh. Chem., 138, 569 (2007).
B.M. Wei, Z.Y. Zhang, Z.Q. Dai and K.C. Zhang, Monatsh. Chem., 142, 1029 (2011).
E. Janus, L. Goc-Maciejewska, M. Lozynski and J. Pernak, Tetrahedron Lett., 47, 4079 (2006).
H. Guo, J.L. Wang, X. Li, D.S. Lv and X.F. Lin, Chin. J. Catal., 32, 162 (2011).
B.J. Cox, S. Jia, Z.C. Zhang and J.G. Ekerdt, Polym. Degrad. Stab., 96, 426 (2011).
J. Buckingham, Dictionary of Organic Compounds, Routledge, New York (1982).
N.L. Lancaster, T. Weltib and G.B. Yong, J. Chem. Soc., Perkin Trans. II, 2267 (2001)