7
96
SALECHI et al.
Perkin Elmer 240 Mc. The purity of compounds was
checked and the reaction progress was monitored by
GLC on a gas chromatograph Shimadzu GC 8A
equipped with a flame-ionization detector, or by TLC
on silica gel plates (SIL G/UV 254, Merck).
alcohol (2 mmol) and iron(III) perchlorate on silica
gel (2.34 3.9 g corresponding to 0.6 1.0 mmol of
3
+
Fe ) was stirred at reflux in 6 ml of ethyl acetate or
ethyl formate for a period required for completion of
the reaction (TLC monitoring). The solvent was
removed in a vacuum, to the residue was added ethyl
ether (50 ml). The mixture was filtered, and the
filtrate was dried on Na SO . Then it was evaporated
Iron(III) perchlorate on silica gel. A solution of
1
g of Fe(ClO ) in 10 ml of ethanol was added to
4 3
2
4
a suspension of 10 g of silica gel (Merck, Kieselgel
0, 70 230 mesh) in 30 ml of ethanol. The mixture
and passed through a short column packed with silica
gel. Esters were obtained in 65 92% yield.
4
was stirred for 30 min and evaporated in a vacuum.
The brown powder obtained was further dried in a
vacuum drying cabinet at 60 C and reduced pressure
The authors are grateful to the Scientific Council
of the Razi University for financial support.
(
20 mm Hg).
REFERENCES
Epoxides alcoholysis. Iron(III) perchlorate on
1
. Smith,
J.C.,
Synthesis,
1994,
p.
629.
silica gel (0.08 1.16 g) containing 0.02 0.3 mmol of
3
+
2. Bonini, C. and Righi, G., Synthesis, 1994, p. 225.
Fe ion was added to a solution of epoxide (2 mmol)
in 7 ml of alcohol. The mixture was stirred at room
temperature for the required time (from 1 min to 8 h).
The reaction was monitored by GLC. Then the mix-
ture was passed through a short column packed with
silica gel and backwashed with ethyl ether (50 ml).
The ether solution was dried on CaCl and evaporated
in a vacuum to obtain the corresponding -alkoxy-
alcohol of high purity in 75 96% yield.
3
. Kino, T., Hatanaka, H., Hashimoto, M., Nishisy-
ma, M., Goto, T., Okuhara, M., Kohsaka, M.,
Aoki, H., and Imanaka, H., J. Antibiot., 1987,
vol. 40, p. 1249.
4
5
6
. Olah, G.A., Fung, A.P., and Meidar, D., Synthesis,
1
981, p. 280.
2
. Iranpoor, N. and Shirini, F., Synth. Commun., 1994,
vol. 24, p. 1959.
. Baker, R.H. and Bordwell, F.G., Org. Synth., 1995,
coll. vol. 3, p. 141.
7. Iqbal, J. and Srivastava, R.R., J. Org. Chem., 1992,
vol. 57, p. 2001.
8. Ishihara, K., Kubote, M., Kurihara, H. and
Yamamoto, H., J. Org. Chem., 1996, vol. 61, p. 4560.
Hydrolysis of epoxides. To a solution of 2 mmol
of epoxide in 7 ml of acetone water mixture (1: 1 by
volume) was added iron(III) perchlorate on silica gel
3
+
(
0.08 0.78 g) containing 0.02 0.2 mmol of Fe ion,
and the reaction mixture was stirred at room tempera-
ture or at reflux. On completion of the reaction the
mixture was passed through a short column packed
with silica gel and backwashed with ethyl ether
9
. Zhang, G.S. Synth. Commun., 1998, vol. 28, p. 1159.
1
1
1
1
0. Parmar, A., Kaur, J., Goyal, R., Kumar, B., and
Kumar, H. Synth. Commun., 1998, vol. 28, p. 2821.
1. Iranpoor, N., Firouzabadi, H., and Zolfigol, M.A.,
Synth. Commun., 1998, vol. 28, p. 1923.
2. Saravanan, P. and Singh, V.K. Tetrahedron Lett.,
999, vol. 40, p. 2611.
3. Otera, J. Chem. Rev., 1993, vol. 93, p. 1449.
14. Ringold, H.J., Loeken, B., Rosenkranz, G., and
Sondheimer, F., J. Am. Chem. Soc., 1956, vol. 78,
p. 816.
(
50 ml). The ether solution was dried on CaCl and
2
evaporated in a vacuum to obtain the corresponding
vicinal diols in 75 95% yield.
1
Esterification of carboxylic acids with alcohols
in the presence of iron(III) perchlorate on silica
gel in dichloromethane. To a solution of alcohol
(
2 mmol) and acid (6 mmol) in 7 ml of dichloro-
methane was added iron(III) perchlorate on silica gel
15. Gramain, J.C. and Remuson, R., Synthesis, 1982,
p. 264.
16. Chavan, S.P., Subbarao, Y.T., Dantale, S.W., and
Sivappa, R. Synth. Commun., 2001, vol. 31, p. 289.
3
+
(
0.2 1.0 mmol of Fe ), and the mixture was stirred
at reflux till the completion of the reaction. Then
0 ml of ether was added and the mixture was filter-
5
1
7. Habibi, M.H., Tangestaninejad, Sh., Mirkhani, V.,
and Yadollahi, B. Tetrahedron, 2001, vol. 57,
p. 8333.
ed. The filtrate was twice washed with 10% water
solution of NaHCO and with water. The organic
3
layer was separated and dried on MgSO . The solvent
4
1
1
2
8. Salehi, P. and Rostamian Motlagh A.M. Synth.
Commun., 2000, vol. 30, p. 671.
was evaporated, the residue was submitted to
chromatography on a short column packed with silica
gel using as eluent hexane ether mixture. Yields of
reaction products were 70 90%.
9. Salechi P., Irandoost M., Seddighi B., and Kargar
BehbahaniF., Synth. Commun., 2000, vol. 30, p. 1743.
0. Salechi, P., Seddighi, B., Irandoost, M., and Kargar
Behbahani, F., Synth. Commun., 2000, vol. 30,
p. 2967.
Acetylation and formylation of alcohols with
ethyl acetate and ethyl formate. A mixture of an
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 6 2003