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020 J. Chin. Chem. Soc., Vol. 54, No. 4, 2007
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999, 181, 217.
was obtained as described above for the unsubstituted ana-
logue.
1
Supported heteropolyacid catalysts were prepared by
4
. Gruffaz, M.; Micaelli, O. USP. 1981, 4275228.
. Dijs, I.-J.; Van Ochten, H.-L.-F.; VanWalree, C.-A.; Geus,
J.-W.; Jenneskens, L.-W. J. Mol. Catal. 2002, 188, 206.
. Cran, R.-A.; Brown, S.-H.; Caul, L.-De. USP. 1999, 5973/
93.
2
impregnating a support in the form of powder (SiO ) with
5
an aqueous solution of the heteropolyacid with different
concentrations. Samples were dried at 120-140 °C, and the
catalysts were calcined at 300 °C in a furnace prior to use.
6
7
8
9
. Misono, M.; Okuhara, T. Chemtech. 1993, 23, 23.
. Thomas, J.-M. Scientific American 1992, 266, 112.
. Kozhevnikov, I.-V. Chem. Rev. 1998, 98, 171.
General Procedure
The homogeneous process was performed by adding
10. Izumi, Y.; Urabe, K.; Onak, M. Zeolite. Clay and Heteropoly
5
acetic anhydride (5 mL) to a solution of H14-P (0.2 g) and
Acids in Organic Synthesis; Kodansha/VCH: Tokyo, 1992; p
salicylic acid (2 g) at room temperature with stirring. The
heterogeneous reactions were performed by contacting sal-
icylic acid (2 g), acetic anhydride (5 mL) with 0.05 g of
3
11.
1
1. Okuhara, T.; Mizuno, N.; Misono, M. Adv. Catal. 1996, 41,
113.
1
1
2. Harrup, M.-K.; Hill, C.-L. Inorg. Chem. 1994, 33, 5448.
3. Fox, M.-A.; Cardona, R.; Gaillard, E. J. Am. Chem. Soc.
1
5 2
0-50% H14-P /SiO at room temperature for the men-
tioned time with intense stirring. At the end of reaction, the
mixture was diluted with 50 mL of water, and the crude
product was precipitated in an ice bath. The crude product
was removed and after the usual work up, the resulting
solid was washed with cold water and recrystallized in
ethyl acetate. The product was characterized by compari-
1
987, 109, 6347.
1
1
4. Alizadeh, M.-H.; Harmalker, S.-P.; Jeanenin, Y.; Martin-
Frere, J.; Pope, M.-T. J. Am. Chem. Soc. 1985, 107, 2662.
5. (a) Pavia, D.-L.; Lampman G.-M.; Kriz, G.-S. Introduction
to Organic Laboratory Techniques: A Contemporary Ap-
proach; Philadelphia, 1976; p 27. (b) Miller, J.-A.; Neuzil,
E.-F. Modern Experimental Organic Chemistry; Heath
Lexington, MA, 1982; p 192.
1
son of its spectroscopic (IR, H-NMR, Mass) data, and
melting point with that of an authentic sample. The product
yield was determined quantitatively.
1
6. Pandita, S.; Goyal, S. J. Chem. Educ. 1998, 75, 770.
7. Hu, C.; Hashimoto, M.; Okuhara, T.; Misono, M. J. Catal.
1
1
993, 143, 437.
1
8. Kozhevnikov, I.-V. Russ. Chem. Rev. 1987, 56, 811.
9. (a) Bamoharram, F.-F.; Roshani, M.; Heravi, M.-M.; Gahangir,
M.; Gharib, A. Appl. Catal. 2006, 302, 42. (b) Alizadeh,
M.-H.; Razavi, H.; Farrash Bamoharram, F.; Hassanzadeh,
M.-H. Kinet. Catal. 2003, 44, 524.
CONCLUSIONS
1
Preyssler catalyst is an effective solid acid catalyst for
preparation of aspirin. Among various forms of Preyssler
2
2
2
0. Bamoharram, F.-F.; Roshani, M.; Alizadeh, M.-H.; Razavi,
H.; Moghayadi, M. J. Brazilian Chem. Soc. 2006, 17, 505.
1. Alizadeh, M.-H.; Razavi, H.; Bamoharram, F.-F.; Daneshvar,
K. J. Mol. Catal. 2003, 206, 89.
5
catalyst used, the H14-P shows higher activity than the
other forms of Preyssler, as well as Keggin types and sulfu-
ric acid. This method demonstrates the applicability of
Preyssler’s anion for some reactions that require a solid cat-
alyst, with strong acidic properties, highly thermal stability
and functionality over a wide range of pH. In addition, sim-
ple experimental setup and procedure makes this method a
useful addition to the present methodologies.
2. (a) Bamoharram, F.-F.; Heravi, M.-M.; Roshani, M.; Gharib,
A.; Jahangir, M. J. Mol. Catal. 2006, 252, 90. (b) Heravi,
M.-M.; Motamedi, R.; Seifi, N.; Bamoharram, F.-F. J. Mol.
Catal. 2006, 252, 1. (c) Heravi, M.-M.; Derikvand, F.;
Bamoharram, F.-F. J. Mol. Catal. 2005, 242, 173. (d) Heravi,
M.-M.; Bakhtiari, Kh.; Bamoharram, F.-F. Catal. Commun.
2
006, 7, 373. (e) Heravi, M.-M.; Bakhtiari, Kh.; Bamoharram,
F.-F. Catal. Commun. 2006, 7, 499. (f) Heravi, M.-M.;
Derikvand, F.; Bamoharram, F.-F. Synth. Commun. 2006, in
press. (g) Bamoharram, F.-F.; Heravi, M.-M.; Roshani, M.;
Akbarpour, M. J. Mol. Catal. 2006, 255, 193. (h) Heravi,
M.-M.; Behbahani, F.-K.; Bamoharram, F.-F. J. Mol. Catal.
Received August 2, 2006.
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