Natural Kaolin supported sulfuric acid as an efficient catalyst for the preparation of 1, 1-diacetates under solvent-free conditions

Iranian Journal of Catalysis

مقاله 4، دوره 1، شماره 1، شهریور 2011، صفحه 25-29   

نویسندگان

Zinat Gordi^{* 1}؛ Hossein Eshghi²

¹Department of Chemistry, Payame Noor University, Torbat-e-Heydarieh, Iran.

²Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad, 91775-1436, Iran.

چکیده

A facile and efficient method for the preparation of 1,1-diacetates of aldehydes is improved. The acidified kaolin with sulfuric acid (2 % w/w) catalyzed 1,1-diacetates formation from aldehydes in solvent-free conditions. Both aromatic and aliphatic aldehydes gave high yields (85-95 %) of the corresponding 1, 1-diacetates. Advantages of this method are the use of inexpensive and selective catalyst, with high yields in simple operation, and short reaction time under solvent-free conditions.

کلیدواژه‌ها

Aldehydes؛ 1,1-Diacetates؛ Kaolin؛ Protection؛ Solvent-free

مراجع

[1] T.W. Green, P.G.M. Wuts, Protective Groups in Organic Synthesis. 3rd ed. John Wiley, New York, 1999, p. 306-307.

[2] S.M. Lukyanov, A.V. Koblik, Russ. Chem. Rev. 65 (1996) 3-28.

[3] L.K. Sydnes, G.S. Pedersen, B. Holmelid, M. Sandberg, Synthesis (2007) 3692-3696.

[4] H. Held, A. Rengstle, D. Mayer, Ullmann,s Encyclopedia of Industrial Chemistry Vol A1: 5th ed., W. Gerhartz, Ed. VCH, New York, p 68.

[5] R. Wedscheider, E. Spath, Monatsh. Chem. 30 (1909) 825 and 840.

[6] F. Freeman, E.M. Karchevski, J. Chem. Eng. Data 22 (1977) 355.

[7] G.A. Olah, A.K. Mehrotra, Synthesis (1982) 962.

[8] (a) I. Scriabine, Bull. Soc. Chim. Fr. (1961) 1194.

(b) F.O. Cockerlle, U S Patent (1941) 2264789; Chem. Abst. 36 (1941) 1620.

[9] K.S. Kochhar, B.S. Bal, R.P.N. Rajadhyaksha, H.W. Pinnick, J. Org. Chem. 48 (1983) 1765.

[10] N. Deka, D.J. Kalita, R. Borah, J.C. Sarma, J. Org. Chem. 62 (1997) 1563.

[11] J.K. Michie, J.A. Miller, Synthesis (1981) 824.

[12] (a) C. Pereira, B. Gigante, M.J.M. Curto, H. Carreyre, G. Perot, M. Guisnet, Synthesis (1995) 1077. (b) P. Kumar, V.R. Hegde, T.P. Kumar, Tetrahedron Lett. 36 (1995) 601.

[13] S.V.N. Raju, J. Chem. Res. (S) (1996) 68.

[14] (a) H. Eshghi, Z. Gordi, Phosphorus Sulfur Silicon 179 (2004) 1341-1346. (b) T.S. Li, Z.H. Zhang, Y.J. Gao, Synth. Commun. 28 (1998) 4665. (c) Z.H. Zhang, T.S. Li, C.G. Fu, J. Chem. Res. (S) (1997) 174.

[15] T.S. Jin, G.Y. Du, Z.H. Zhang, T.S. Li, Synth. Commun. 27 (1997) 2261.

[16] N. Deka, R. Borah, D.J. Kalita, J.C. Sarma, J. Chem. Res. (S) (1998) 94.

[17] V.K. Aggrawall, S. Fonquerna, G.P. Vennall, Synlett. (1998) 849.

[18] B. Karimi, H. Seradj, G.R. Ebrahimian, Synlett (2000) 623.

[19] Y.Q. Li, Synth. Commun. 30 (2000) 3913.

[20] T.S. Jin, Y.R. Ma, X. Su, D. Liang, T.S. Li, J. Chem. Res. (S) (2000) 96.

[21] J.R. Satam, R.V. Jayaram, Cat. Commun. 8 (2007) 1414-1420.

[22] B.R. Jermy, A. Pandurangan, Cat. Commun. 9 (2008) 577-583.

[23] J.R. Satam, R.V. Jayaram, Synth. Commun. 38 (2008) 592-602.

[24] (a) M.B.A. Rahman, S.M. Tajudin, M.Z. Hussein, R.N.Z.R.A. Rahman, A.B. Salleh, M. Basri, Appl. Clay Sci. 29 (2005) 111-116. (b) G. Nagendrappa, Appl. Clay Sci. 50 (2010) in press.

[25] V.R. Choudhary, K. Mantri, S.K. Jana, Catal. Commun. 2 (2001) 57–61.

[26] P.K. Igbokwe, V.I. Ugonabo, N.A. Iwegbu, P.C. Akachukwu, C.J. Olisa, J. Univ. Chem. Technol. Metall. 43 (2008) 345–348.

[27] N. Bizaia, E.H. de Faria, G.P. Ricci, P.S. Calefi, E.J. Nassar, K.A.D.F. Castro, S. Nakagaki, K.J. Ciuffi, R. Trujillano, M.A. Vicente, A. Gil, S.A. Korili, Appl. Mater. Interfaces 1 (2009) 2667–2678.

[28] H.A. Dabbagh, A. Teimouri, A. Najafi Chermahini, Appl. Catal. 76 (2007) 24–33.

[29] J. Bucking, S.M. Donghy, Dictionary of Organic Compounds. Chapman and Hall, New York, 5th ed. 1982.