ORDER
REPRINTS
1
806
GHIACI AND BAKHTIARI
EXPERIMENTAL
Typical procedure for the dehydration of aldoximes: A solution of
p-chlorobenzaldehyde oxime (1.16 g, 7.5 mmol), p-toluenesulfonyl chloride
2.86 g, 15 mmol) and pyridine (1.2 mL, 15 mmol) in CHCl (20 mL) was
(
3
mixed with 3 g alumina and concentrated under vacuum to give a yellowish
solid. The mixture was introduced in a Pyrex flask and submitted to micro-
wave irradiation. After completion of the reaction (TLC, 3–15 min) 50 mL
CH OH was added. The mixture was filtered and concentrated. To the
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crude mixture, chloroform (25 mL) was added. The filtrate was washed
with brine (2 ꢁ 25 mL), and then with 2 ꢁ 25 mL of 5% sodium bicarbonate.
The collected organic phase was dried with MgSO , filtered and evaporated
4
to give the crude product with good chemical purity. Flash chromato-
graphy (cyclohexane–ethyl acetate) gave analytically pure sample in 64%
ꢀ
(
m.p. 89–90 C) isolated yield.
4
-Chlorobenzonitrile: IR (KBr): 2250 (m), 1630 (w), 1580 (m), 1480 (s),
ꢂ1
1
380 (s), 1080 (m), 820 (s), 780 (w), 750 (m), 700 (m), 680 (m), 550 (m) cm
.
1
H-NMR (CDCl , TMS): d, 7.56 (dd, 4H, J ¼ 6 Hz) ppm.
3
4
-Bromobenzonitrile: IR (KBr): 2250 (s), 1580 (s), 1480 (s), 1380 (m),
ꢂ1
1
1
060 (s), 820 (s), 770 (m), 700 (w), 550 (s) cm . H-NMR (CDCl , TMS): d,
3
7
.6 (dd, 4H, J¼3 Hz) ppm.
2,6-Dichlorobenzonitrile:IR(KBr):3020(m),2250(s),1680(w),1570(w),
550 (w), 1430 (s), 1220 (s), 1100 (m), 980 (w), 800 (m), 780 (s) cm . H-NMR
ꢂ1 1
1
(
CDCl , TMS): d, 7.45 (s, 3H) ppm.
3
3,4,5-Trimethoxybenzonitrile: IR (KBr): 2880 (m), 2250 (s), 1580 (s),
520 (s), 1460 (m), 1340 (s), 1240 (s), 1140 (s), 1000 (s), 960 (m), 860 (s), 820
1
(
ꢂ1
1
s), 780 (m), 745 (w), 700 (w), 630 (s) cm . H-NMR (CDCl , TMS): d, 6.9
3
(
s, 2H), 3.78 (s, 6H), 3.74 (s, 3H) ppm.
2-Hydroxybenzonitrile: IR (KBr): 3020 (m), 2250 (s), 2080 (w),
990 (m), 1950 (m), 1915 (m), 1660 (s), 1570 (w), 1480 (s), 1450 (s), 1370 (s),
1
1
ꢂ1 1
290 (s), 1080 (s), 1030 (m), 1015 (w), 960 (s), 910 (s), 590 (s) cm . H-NMR
(
CDCl , TMS): d, 8.93–7.18 (m, 4H), 2.48 (s, 1H) ppm.
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ACKNOWLEDGMENT
This work is financially supported by IUT, Isfahan, Iran.
REFERENCES
1. (a) Friedrich, K.; Wallenfels, K., in Rappoport ‘‘The Chemistry of the
Cyano Group’’; Wiley; New York, 1970, pp. 92–96; (b) Molina, P.;