Document Type : Short communication

Authors

1 payame noor university

2 Faculty of Chemistry, Bu-Ali Sina University, P.O. BOX 651783868, Hamedan, Iran

3 Department of Chemistry, Payame Noor University (PNU), P.O. BOX 19395-3697 Tehran, Iran

4 Young Researchers and Elite Club, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran

Abstract

A convenient approach for oxidation of structurally diverse alcohols has been developed using KMnO4 as oxidant agent in the presence of a catalytic amount of Al2O3 in aqueous acetonitrile. In this method various alcohols generally afforded the corresponding carbonyl compounds directly in good to high yield under ultrasound irradiation conditions. It shows that this kind of catalysis system is very active, selective and suitable for oxidation of benzylic alcohols. Furthermore, all products were obtained through a simple filtration and washed with solvent, and there was no need for column chromatography. All products have been characterized by IR and 1HNMR spectral data.

Graphical Abstract

Ultrasound assisted oxidation of various alcohols to corresponding aldehydes by using Al2O3 as catalyst

Keywords

Main Subjects

[1] (a) J.C. Colmenares, W. Ouyang, M. Ojeda, E. Kuna, O. Chernyayeva, D. Lisovytskiy, S. De, R. Luque, A.M. Balu, Appl. Catal., B., 2016, 183, 107-112. (b) X. Lang, W. Ma, C. Chen, H. Ji, J. Zhao, Acc. Chem. Res., 2014, 47, 355–363. (c) A. Maldotti, A. Molinari, R. Amadelli, Chem. Rev., 2002, 102, 3811–3836.
[2] X.J. Meng, K.F. Lin, X.Y. Yang, Z.H. Sun, D.Z. Jiang, F.S. Xiao, J. Catal., 2003, 218, 460-464.
[3] G. Ferguson, A.N. Ajjou, Tetrahedron Lett., 2003, 44, 9139-9144.
[4] F. Zaera, J. Catal. Today, 2003, 81,149-157.
[5] K.O. Xavier, J. Chacko, K.K. Mohammad Yusuff, J. Mol. Catal. A: Chem., 2002, 178, 275-281.
[6] S. Das, T. Punniyamurthy, Tetrahedron Lett., 2003, 44, 6033-6035.
[7] I. Fernandez, J.R. Pedro, A.L. Rosello, R. Ruiz, I. Castro, X. Ottenwaelder, Y. Journaux, Eur. J. Org. Chem., 2001, 7, 1235-1247.
[8] J.E. Remias, A. Sen, J. Mol. Catal. A: Chem., 2002, 189, 33-38.
[9] Y. Shvo, V. Goldman-Lev, J. Organomet. Chem., 2002, 650, 151-156.
[10] T.L. Stuchinskaya, I.V. Kozhevnikov, J. Catal. Commun., 2003, 4, 417-422.
 
 
 
[11] J. Brinksma, M.T. Rispens, R. Hage, B.L. Feringa, J. Inorg. Chim. Acta., 2002, 337, 75-82.
[12] J. Fatiadi, Synthesis, 1978, 85-127.
[13] L.F. Fieser, M. Fieser, Reagents for Organic Synthesis, Wiley, New York, 1967, 1, 942-952.
[14] M.F. Mady, A.A. El-Kateb, I.F. Zeid, K.B. Jorgensen, Journal of chemistry, 2013, Article ID 364036.
[15] S.L. Regen, C. Koteed, J. Am. Chem. Soc., 1977, 99, 3837-3838.
[16] F.M. Menger, C.J. Lee, J. Org. Chem., 1979, 44, 3446-3448.
[17] N.A. Noureldin, D.G. Lee, Tetrahedron Lett., 1981, 22, 4889-4890.
[18] J.-D. Lou, W.-X. Lou, J. Synth. Commun., 1997, 27, 3697-3699.
[19] R. Sreekumar, R. Padmakumar, Tetrahedron Lett., 1997, 38, 5143-5146.
[20] H. Firouzabadi, M. Fakoorpour, H. Hazarkhani, J. Synth. Commun., 2001, 31, 3859-3862.
[21] A. Rostami, M. Mahboubifar, A. Khazaei, S. Afr. J. Chem., 2008, 61, 9-12.
[22] A. Khazaei, A. Raiatzadeh, A. Rostami, J. Chin. Chem. Soc., 2007, 54, 465-468.
[23] A. Khazaei, E. Mehdipour, S. Yadegari, J. Phosphorus, Sulfur Silicon Relat. Elem., 2004, 179, 437-441.
[24] R. Ghorbani-Vaghei, A.Khazaei, Tetrahedron Lett., 2003, 44, 7525-7527.