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Methoxymethylation of Substituted Alcohols using Dimethoxymethane over Mo(VI)/ZrO2
Corresponding Author(s) : S.Z. Mohamed Shamshuddin
Asian Journal of Chemistry,
Vol. 30 No. 3 (2018): Vol 30 Issue 3
Abstract
The methoxymethylation reaction of alcohols was studied on Mo/ZrO2 (MZ) catalysts. The catalyst containing 5, 10 and 15 % Mo(VI) ions was prepared by solution combustion method. These solid acid catalytic materials were characterized by NH3-TPD, powder XRD, BET, FTIR spectroscopy, scanning electron microscopy, transmission electron spectroscopy and ICP-OES techniques. These catalysts were evaluated for their catalytic activity in the synthesis of methoxymethylation reactions of various substituted alcohols with dimethoxymethane in shorter reaction times (20 min) at moderate temperature (40 °C) with excellent yields (around 99 %). The main features of the Mo/ZrO2 catalyzed reaction are high yields, ease of scale up to gram scale, recyclable catalysts, inexpensive reagents, eco-friendly catalysts and a solvent free approach for the synthesis of methoxymethylated products.
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A. Corma, S. Iborra, S. Miquel and J. Primo, Catal., 173, 315 (1998); https://doi.org/10.1006/jcat.1997.1930.
X. Song and A. Sayari, Catal. Rev., Sci. Eng., 38, 329 (1996); https://doi.org/10.1080/01614949608006462.
T. Yamaguchi, Catal. Today, 20, 199 (1994); https://doi.org/10.1016/0920-5861(94)80003-0.
P.D.L. Mercera, Ph.D. Thesis, Twente Institute of Technology, Netherland (1991).
J. Nawrocki, M. Rigney, A. McCormick and P.W. Carr, J. Chromatogr. A, 657, 229 (1993); https://doi.org/10.1016/0021-9673(93)80284-F.
B.M. Reddy and A. Khan, Catal. Rev., Sci. Eng., 47, 257 (2005); https://doi.org/10.1081/CR-200057488.
M. Vrinat, D. Hamon, M. Breysse, B. Durand and T. des Courieres, Catal. Today, 20, 273 (1994); https://doi.org/10.1016/0920-5861(94)80006-5.
E. Iglesia, D.G. Barton, S.L. Soled, S. Miseo, J.E. Baumgartner, W.E. Gates, G.A. Fuentes and G.D. Meitzner, Stud. Surf. Sci. Catal., 101, 533 (1996); https://doi.org/10.1016/S0167-2991(96)80264-3.
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B.M. Reddy and P.M. Sreekanth, Synth. Commun., 32, 2815 (2002); https://doi.org/10.1081/SCC-120006465.
B.M. Reddy, M.K. Patil and B.T. Reddy, Catal. Lett., 125, 97 (2008); https://doi.org/10.1007/s10562-008-9518-1.
C. Martin, I. Martin and V.J. Rives, Chem. Soc. Faraday. Trans., 89, 4131 (1993); https://doi.org/10.1039/ft9938904131.
M. Niwa, H. Yamada and Y. Murakami, J. Catal., 134, 331 (1992); https://doi.org/10.1016/0021-9517(92)90232-7.
Y. Matsuoka, M. Niwa and Y. Murakami, J. Phys. Chem., 86, 1477 (1990); https://doi.org/10.1021/j100367a051.
H. Miyata, S. Tokuda, T. Ono, T. Ohno and F. Hatayama, J. Chem. Soc., Faraday Trans., 86, 2291 (1990); https://doi.org/10.1039/ft9908602291.
T.W. Greene and P.G.M. Wuts, Protective Groups in Organic Synthesis, Wiley: New York, edn 2 (1991).
T.S. Jin, T.S. Li and Y.T. Gao, Synth. Commun., 28, 837 (1998); https://doi.org/10.1080/00032719808006481.
B.C. Ranu, A. Majee and A.R. Das, Synth. Commun., 25, 363 (1995); https://doi.org/10.1080/00397919508011367.
P. Kumar, S.V.N. Raju, R.S. Reddy and B. Pandey, Tetrahedron Lett., 35, 1289 (1994); https://doi.org/10.1016/0040-4039(94)88046-8.
M.I. Kantam and P.L. Santhi, Synlett, 429 (1993); https://doi.org/10.1055/s-1993-22483.
H.K. Patney, Synlett, 567 (1992); https://doi.org/10.1055/s-1992-21417.
B.P. Bandgar, C.T. Hajare and P.P. Wadgaonkar, J. Chem. Res. (S), 90 (1990).
C.H. Lin, M.Y. Wan and Y.M. Huang, Catal. Lett., 87, 253 (2003); https://doi.org/10.1023/A:1023472029190.
B. Sreedhar, V. Swapna and Ch. Sridhar, Catal. Commun., 6, 293 (2005); https://doi.org/10.1016/j.catcom.2005.02.003.
B. Karimi and L, Ma'mani, Tetrahedron Lett., 44, 6051 (2003); https://doi.org/10.1016/S0040-4039(03)01481-3.
F. Shirini, M.A. Zolfigol and J. Albadi, Synth. Commun., 40, 910 (2010); https://doi.org/10.1080/00397910903026707.
T.-S. Jin, J.-J. Guo, Y.-H. Yin, S.-L. Zhang and T.-S. Li, J. Chem. Res., 188 (2002); https://doi.org/10.3184/030823402103171627.
J.R. Sohn, E.W. Chun and Y. I. Pae, Bull. Korean Chem. Soc., 24, 1785 (2003); https://doi.org/10.5012/bkcs.2003.24.12.1785.
K.C. Patil, M.S. Hegde, T. Rattan and S.T. Aruna, Chemistry of Nanocrystalline Oxide Materials: Combustion Synthesis, Properties and Applications, World Science Publishing Pvt. Ltd.: Singapore (2008).
K. Tanabe, M. Misson, Y. Ono and J. Hattori, New Solid Acids and Bases, Elsevier Science, Amsterdam (1989).
A.H. Zapien, J.M.H. Enriquez, R.G. Alamilla, G.S. Robles, U.P. Garcia and L.A.G. Serrano, Adv. Mater. Sci. Eng., Article ID 43203 (2014); https://doi.org/10.1155/2014/432031.
S.Z.M. Shamshuddin, M. Shyamsundar, N. Thimmaraju, Venkatesh, G. Vatsalya and M.Senthilkumar, Comptes Rend. Chem., 15, 799 (2012); https://doi.org/10.1016/j.crci.2012.05.020.
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