1
602
SHIRINI et al.
EXPERIMENTAL
Commercial reagents from Fluka, Merck, Riedel-
REFERENCES
1. Trost, B.M., Comprehensive Organic Synthesis
(Oxidation), New York: Pergamon, 1991, vol. 7.
dehaen AG, and Aldrich chemical companies were
used. The oxidation products were identified by com-
2
.
Warnhoff, E.W., Mortin, D.G., and Jonson, W.S.,
Org. Synth., 1963, vol. 40, p. 162.
1
paring their spectral (IR and H NMR), TLC, and
physical parameters with those reported for authentic
samples [9, 10].
Oxidation of 4-chlorobenzyl alcohol (Ic) to
-chlorobenzaldehyde (IIc) (general procedure).
a. 4-Chlorobenzyl alcohol (Ic), 0.253 g (2 mmol), was
added to a suspension of 1.76 g (10 mmol) of HIO3,
3
.
House, H.O., Modern Synthetic Reactions, Menlo
Park, CA: W.A. Benjamin, 1972, 2nd ed., pp. 257
2
91.
Firouzabadi, H. and Shirini, F., Synth. Commun.,
996, vol. 26, p. 423.
Firouzabadi, H. and Shirini, F., Synth. Commun.,
996, vol. 26, p. 1065.
4
4
5
.
.
1
0
.6 g of wet SiO (50 wt %), and 0.378 g (1.5 mmol)
2
1
of (NH ) Cr O in 6 ml of hexane, the mixture was
4
2
2
7
stirred for 45 min at room temperature (the progress
of the reaction was monitored by TLC) and filtered,
and the precipitate was washed with methylene
chloride (2 5 ml). The washings were combined with
the filtrate, treated with 4 g of anhydrous MgSO4
6. Firouzabadi, H., Iranpoor, N., and Zolfigol, M.A.,
Synth. Commun., 1998, vol. 28, p. 377.
7
8
9
.
.
.
Firouzabadi, H., Iranpoor, N., and Zolfigol, M.A.,
Synth. Commun., 1998, vol. 28, p. 1179.
Iranpoor, N., Firouzabadi, H., and Zolfigol, M.A.,
Synth. Commun., 1998, vol. 28, p. 367.
(
20 min), and the drying agent was filtered off.
Evaporation of the solvent, followed by column
chromatography on silica gel, gave 0.212 g (85%) of
Firouzabadi, H., Iranpoor, N., and Zolfigol, M.A.,
Bull. Chem. Soc. Jpn., 1998, vol. 71, p. 2169.
4-chlorobenzaldehyde (IIc).
1
0. Iranpoor, N., Firouzabadi, H., and Zolfigol, M.A.,
b. Without a solvent. 4-Chlorobenzyl alcohol (Ic),
.253 g (2 mmol), was added to a mixture of 1.76 g
Bull. Chem. Soc. Jpn., 1998, vol. 71, p. 905.
0
(
10 mmol) of HIO , 0.6 g of wet SiO (20 wt % of
11. Zolfigol, M.A., Iranpoor, N., and Firouzabadi, H.,
3
2
water), and 0.378 g (1.5 mmol) of (NH ) Cr O , and
Orient. J. Chem., 1998, vol. 14, p. 369.
4
2
2
7
the mixture was shaken for 10 min at room tempera-
ture (the progress of the reaction was monitored by
TLC). The mixture was treated with 2 5 ml of
12. Firouzabadi, H., Iranpoor, N., and Zolfigol, M.A.,
Iran J. Chem. Chem. Eng., 1997, vol. 16, p. 48.
1
1
1
1
3. Firouzabadi, H., Iranpoor, N., and Zolfigol, M.A.,
CH Cl and filtered. The filtrate was treated with 4 g
2
2
Synth. Commun., 1997, vol. 27, p. 3301.
of anhydrous MgSO (20 min), and the drying agent
4
4. Iranpoor, N., Firouzabadi, H., and Zolfigol, M.A.,
was filtered off. The solvent was removed from the
filtrate, and the residue was subjected to column
chromatography on silica gel to obtain 0.224 g (90%)
of 4-chlorobenzaldehyde (IIc).
The authors are gratefull to the research affairs,
Gilan University (Rasht, Iran) and Bu-Ali Sina
University (Hamadan, Iran) for the financial support
of this work.
Synth. Commun., 1998, vol. 28, p. 2773.
5. Zolfigol, M.A., Synth. Commun., 1999, vol. 29,
p. 905.
6. Zolfigol, M.A., Nematollahi, D., and Mallack-
pour, S.E., Synth. Commun., 1999, vol. 29, p. 2277.
17. Zolfigol, M.A. and Mallackpour, S.E., Synth.
Commun., 1999, vol. 29, p. 4061.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 11 2001