Vol. 22, No. 7, 2011
Farhadi et al.
1331
which is a moderately reactive nucleophile, resulting in
the formation of the corresponding acetate and acetic acid
(Scheme 1).
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Scheme 1. Proposed catalytic cycle for the acetylation reaction over HPA.
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J. Org. Chem. 1998, 63, 2342.
According to this mechanism, the higher reactivity
of alcohols and the selective acetylation of an alcohol in
the presence of a phenol could be related to the higher
nucleophilicity of the oxygen atom of the alcoholic OH
group.
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1743.
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Conclusions
A new V-containing HPA with nanosized particles was
prepared by the hydrothermal process. The nano nature of
its particles was confirmed by XRD and TEM results. This
HPA was used as a new recyclable heterogeneous catalyst
for the acetylation of alcohols and phenols with acetic
anhydride under solvent-free conditions. Various hydroxy
groups can be efficiently converted into their corresponding
acetates with very short reaction times. The catalyst
can be used for subsequent cycles of acetylation without
observable loss of activity. For all the examples studied,
this simple method eliminates completely the necessity of
using organic solvents in the reaction.
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P.; Chem. Rev. 2004, 104, 199.
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2007, 274, 1.
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22. Shirini, F.; Zolfigol, M. A.; Mohammadi, K.; Bull. Korean
Chem. Soc. 2004, 25, 325.
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Commun. 2003, 764.
Acknowledgments
24. Chavan, S. P.; Anand, R.; Pasupathy, K.; Rao, B. S.; Green
Chem. 2001, 3, 320; Kumareswaran, R.; Pachamuthu, K.;
Vankar, Y. D.; Synlett 2000, 1652.
The financial support from the Lorestan University
Research Council for this work is greatly appreciated.
25. Chakraborti, A. K.; Gulhane, R.; Tetrahedron Lett. 2003, 44,
3521.
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