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Pyridinium Chlorochromate Catalyzed Oxidation of Toluenes to Aromatic Carboxylic Acids with Molecular Oxygen in Sub-critical Water
Corresponding Author(s) : Recep Ozen
Asian Journal of Chemistry,
Vol. 26 No. 3 (2014): Vol 26 Issue 3
Abstract
Oxidation of substituted toluenes in the presence of molecular oxygen with pyridinium chlorochromate in subcritical water under the nitrogen atmosphere at 120 °C to the corresponding substituted benzoic acids were investigated. Substituted toluenes were directly oxidized to their carboxylic acids in excellent yields (> 70 %).
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- F. Yang, J. Sun, Z. Zheng, W. Qiu, J. Tang and M. He, Tetrahedron, 60, 1225 (2004); doi:10.1016/j.tet.2003.11.079.
- M. Gupta, S. Paul, R. Gupta and A. Loupy, Tetrahedron Lett., 46, 4957 (2005); doi:10.1016/j.tetlet.2005.05.104.
- S. Yamazaki, Synth. Commun., 29, 2211 (1999); doi:10.1080/00397919908086219.
- W.S. Trahanovsky and L.B. Young, J. Org. Chem., 31, 2033 (1966); doi:10.1021/jo01344a544.
- E. Ganin and I. Amer, Synth. Commun., 25, 3149 (1995); doi:10.1080/00397919508015465.
- T. Nishimura, Org. Synth., 36, 58 (1956).
- H. Kaplan, J. Am. Chem. Soc., 63, 2654 (1941); doi:10.1021/ja01855a038.
- V.V. Richter, Chem. Ber., 19, 1060 (1886); doi:10.1002/cber.188601901236.
- L. Syper, Tetrahedron Lett., 8, 4193 (1967); doi:10.1016/S0040-4039(01)89720-3.
- R.L. Holliday, B. Y.M. Jong and J.W. Kolis, J. Supercrit. Fluids, 12, 255 (1998);doi:10.1016/S0896-8446(98)00084-9.
- Y. Yoshino, Y. Hayashi, T. Iwahama, S. Sakaguchi and Y. Ishii, J. Org. Chem., 62, 6810 (1997); doi:10.1021/jo9708147.
- G. Cainelli and G. Cardillo, Chromium Oxidation in Organic Chemistry, Springer-Verlag, Berlin, p. 118 (1984).
- B. Kayan, R. Ozen, A.M. Gizir and N.S. Kus, Org. Prep. Proced. Int., 37, 83 (2005);doi:10.1080/00304940509355405.
- P.J. Gemperline, Y. Yang and Z. Bian, Anal. Chim. Acta, 485, 73 (2003); doi:10.1016/S0003-2670(03)00354-4.
- D. Tromans, Ind. Eng. Chem. Res., 39, 805 (2000); doi:10.1021/ie990577t.
- R.C. Weast and M.J. Astle, Handbook of Data on Organic Compounds CRC Boca Raton, FL (1985).
References
F. Yang, J. Sun, Z. Zheng, W. Qiu, J. Tang and M. He, Tetrahedron, 60, 1225 (2004); doi:10.1016/j.tet.2003.11.079.
M. Gupta, S. Paul, R. Gupta and A. Loupy, Tetrahedron Lett., 46, 4957 (2005); doi:10.1016/j.tetlet.2005.05.104.
S. Yamazaki, Synth. Commun., 29, 2211 (1999); doi:10.1080/00397919908086219.
W.S. Trahanovsky and L.B. Young, J. Org. Chem., 31, 2033 (1966); doi:10.1021/jo01344a544.
E. Ganin and I. Amer, Synth. Commun., 25, 3149 (1995); doi:10.1080/00397919508015465.
T. Nishimura, Org. Synth., 36, 58 (1956).
H. Kaplan, J. Am. Chem. Soc., 63, 2654 (1941); doi:10.1021/ja01855a038.
V.V. Richter, Chem. Ber., 19, 1060 (1886); doi:10.1002/cber.188601901236.
L. Syper, Tetrahedron Lett., 8, 4193 (1967); doi:10.1016/S0040-4039(01)89720-3.
R.L. Holliday, B. Y.M. Jong and J.W. Kolis, J. Supercrit. Fluids, 12, 255 (1998);doi:10.1016/S0896-8446(98)00084-9.
Y. Yoshino, Y. Hayashi, T. Iwahama, S. Sakaguchi and Y. Ishii, J. Org. Chem., 62, 6810 (1997); doi:10.1021/jo9708147.
G. Cainelli and G. Cardillo, Chromium Oxidation in Organic Chemistry, Springer-Verlag, Berlin, p. 118 (1984).
B. Kayan, R. Ozen, A.M. Gizir and N.S. Kus, Org. Prep. Proced. Int., 37, 83 (2005);doi:10.1080/00304940509355405.
P.J. Gemperline, Y. Yang and Z. Bian, Anal. Chim. Acta, 485, 73 (2003); doi:10.1016/S0003-2670(03)00354-4.
D. Tromans, Ind. Eng. Chem. Res., 39, 805 (2000); doi:10.1021/ie990577t.
R.C. Weast and M.J. Astle, Handbook of Data on Organic Compounds CRC Boca Raton, FL (1985).