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Zeolite-Assisted Regioselective Nitration of Toluene in Acetonitrile with Nitric Acid/Acetic Anhydride
Corresponding Author(s) : Yanfang Tai
Asian Journal of Chemistry,
Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Abstract
p-Nitrotoluene widely used pharmaceutical and dyestuff intermediates was selectively prepared with nitric acid under the promotion of acetic anhydride in the presence of zeolite catalysts. The ratio of o-nitrotoluene isomer to p-nitrotoluene could reach 0.553 in a moderate total yield of 62.8 % when the reaction was carried out in acetonitrile with 1.89 mmol toluene, 5.67 mmol nitric acid, 5.67 mmol acetic anhydride and 0.13 g HBEA-280 at reflux temperature. The zeolite catalyst has a strong influence on the reaction and could be easily regenerated.
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- G.A. Olah, R. Malhotra and S.C. Narang, Nitration: Methods and Mechanisms, VCH: New York (1989).
- K. Schofield, Aromatic Nitration, University Press: Cambridge (1980).
- M.N. Cortona, N. Vettorazzi, J.J. Silber and L. Sereno, J. Electroanal. Chem., 394, 245 (1995); doi:10.1016/0022-0728(95)04076-Z.
- S. Samajdar, F.F. Becker and B.B. Banik, Tetrahedron Lett., 41, 8017 (2000); doi:10.1016/S0040-4039(00)01397-6.
- M.M. Tasneem, M.M. Ali, K.C. Rajanna and P.K. Saiparakash, Synth. Commun., 31, 1123 (2001); doi:10.1081/SCC-100103545.
- T. Esakkidurai and K. Pitchumani, J. Mol. Catal. Chem., 218, 196 (2004); doi:10.1016/j.molcata.2004.03.047.
- R. Halder, A. Lawal and R. Damavarapu, Catal. Today, 125, 74 (2007); doi:10.1016/j.cattod.2007.04.002.
- X. Peng, H. Suzuki and C. Lu, Tetrahedron Lett., 42, 4357 (2001); doi:10.1016/S0040-4039(01)00750-X.
- R.R. Bak and A.J. Smallridge, Tetrahedron Lett., 42, 6767 (2001); doi:10.1016/S0040-4039(01)01378-8.
- N.S. Chaubal and M.R. Sawant, Catal. Commun., 7, 443 (2006); doi:10.1016/j.catcom.2005.12.017.
- K. Smith, S. Almeer, S.J. Black and C. Peters, J. Mater. Chem., 12, 3285 (2002); doi:10.1039/b204088c.
- X. Peng and H. Suzuki, Org. Lett., 3, 3431 (2001); doi:10.1021/ol016283x.
- P.T. Patil, K.M. Malshe, S.P. Dagade and M.K. Dongare, Catal. Commun., 4, 429 (2003); doi:10.1016/S1566-7367(03)00097-9.
- N. Iranpoor, H. Firouzabadi and R. Heydari, Synth. Commun., 29, 3295 (1999); doi:10.1080/00397919908085957.
- H. Sato and K. Hirose, Appl. Catal. A, 174, 77 (1998); doi:10.1016/S0926-860X(98)00161-6.
- M.A. Zolfigol, E. Madrakian and E. Ghaemi, Molecules, 7, 734 (2002); doi:10.3390/71000734.
- S.M. Kemdeo, V.S. Sapkal and G.N. Chaudhari, J. Mol. Catal. Chem., 323, 70 (2010); doi:10.1016/j.molcata.2010.03.017.
- B. Gigante, A.O. Prazeres, M.J. Marcelo-Curto, A. Cornelis and P. Laszlo, J. Org. Chem., 60, 3445 (1995); doi:10.1021/jo00116a034.
- A. Cornelis, P. Laszlo and P. Pennetreau, J. Org. Chem., 48, 4771 (1983); doi:10.1021/jo00172a062.
References
G.A. Olah, R. Malhotra and S.C. Narang, Nitration: Methods and Mechanisms, VCH: New York (1989).
K. Schofield, Aromatic Nitration, University Press: Cambridge (1980).
M.N. Cortona, N. Vettorazzi, J.J. Silber and L. Sereno, J. Electroanal. Chem., 394, 245 (1995); doi:10.1016/0022-0728(95)04076-Z.
S. Samajdar, F.F. Becker and B.B. Banik, Tetrahedron Lett., 41, 8017 (2000); doi:10.1016/S0040-4039(00)01397-6.
M.M. Tasneem, M.M. Ali, K.C. Rajanna and P.K. Saiparakash, Synth. Commun., 31, 1123 (2001); doi:10.1081/SCC-100103545.
T. Esakkidurai and K. Pitchumani, J. Mol. Catal. Chem., 218, 196 (2004); doi:10.1016/j.molcata.2004.03.047.
R. Halder, A. Lawal and R. Damavarapu, Catal. Today, 125, 74 (2007); doi:10.1016/j.cattod.2007.04.002.
X. Peng, H. Suzuki and C. Lu, Tetrahedron Lett., 42, 4357 (2001); doi:10.1016/S0040-4039(01)00750-X.
R.R. Bak and A.J. Smallridge, Tetrahedron Lett., 42, 6767 (2001); doi:10.1016/S0040-4039(01)01378-8.
N.S. Chaubal and M.R. Sawant, Catal. Commun., 7, 443 (2006); doi:10.1016/j.catcom.2005.12.017.
K. Smith, S. Almeer, S.J. Black and C. Peters, J. Mater. Chem., 12, 3285 (2002); doi:10.1039/b204088c.
X. Peng and H. Suzuki, Org. Lett., 3, 3431 (2001); doi:10.1021/ol016283x.
P.T. Patil, K.M. Malshe, S.P. Dagade and M.K. Dongare, Catal. Commun., 4, 429 (2003); doi:10.1016/S1566-7367(03)00097-9.
N. Iranpoor, H. Firouzabadi and R. Heydari, Synth. Commun., 29, 3295 (1999); doi:10.1080/00397919908085957.
H. Sato and K. Hirose, Appl. Catal. A, 174, 77 (1998); doi:10.1016/S0926-860X(98)00161-6.
M.A. Zolfigol, E. Madrakian and E. Ghaemi, Molecules, 7, 734 (2002); doi:10.3390/71000734.
S.M. Kemdeo, V.S. Sapkal and G.N. Chaudhari, J. Mol. Catal. Chem., 323, 70 (2010); doi:10.1016/j.molcata.2010.03.017.
B. Gigante, A.O. Prazeres, M.J. Marcelo-Curto, A. Cornelis and P. Laszlo, J. Org. Chem., 60, 3445 (1995); doi:10.1021/jo00116a034.
A. Cornelis, P. Laszlo and P. Pennetreau, J. Org. Chem., 48, 4771 (1983); doi:10.1021/jo00172a062.