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. Conclusion
1
[
In conclusion, we have developed an efficient procedure for the
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without use of a catalyst or any other additive. In contrast to the
existing methods using potentially hazardous catalysts/additives,
this new method offers the following competitive advantages: (i)
avoiding the use of any base, metal or Lewis acid catalyst (ii) short
reaction time, (iii) ease of product isolation/purification (iv) high
chemoselectivity, (v) no side reaction, and (vi) low costs and
simplicity in process and handling. The recovered HFIP can be
reusable.
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[
[
4
. Experimental
[
[
General procedure: Alcohol (1 mmol) and NaOCl (ca. 13%, 5 mL)
[
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were dissolved in HFIP (1 mL) and was stirred at 25–30 8C in a vial
for 3 h. After completion of the reaction as indicated by TLC, the
HFIP was separated by distillation and then the mixture was
extracted with diethyl ether (3 Â 25 mL). The combined organic
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2 4
layers were washed with H O and dried over MgSO . The solvent
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chromatography. All the products were characterized by compari-
son of their physical and spectral data with those of authentic
samples. Spectroscopic data for selected examples are shown
below.
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Benzaldehyde (Table 1, entry 1): Oil, IR (KBr): 3064, 2819,
2
À1
1
1
701, 1311 cm
;
3
H NMR (400 MHz, CDCl ): d = 7.52 (t,
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J = 7.54 Hz, 2H), 7.62 (t, J = 7.43 Hz, 1H), 7.87 (d, J = 7.69 Hz, 2H)
13
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0.0 (s, 1H). C NMR: (CDCl
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, 100 MHz): d = 128.8, 129.6, 134.4,
2
1
36.4, 192.3.
[
[
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1
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d
9 8C; IR (KBr): 2727, 1710, 1311 cm ; H NMR (CDCl
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, 100 MHz): = 129.4, 130.8, 134.6, 140.9, 190.8.
-Methoxybenzaldehyde (Table 1, entry 6): Oil; IR (KBr): 2840,
3
, 400 MHz):
1
3
547–548.
C
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(
(
739, 1683 cm ; H NMR CDCl
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CDCl , 100 MHz): = 55.5, 114.2, 129.8, 131.9, 164.5, 190.7.
Acetophenone (Table 1, entry 8): Oil; IR (KBr): 3654, 3062,
3
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3
[
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d
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1
1
685, 1265 cm , H NMR: (400 MHz, CDCl ): d = 2.60 (s, 3H), 7.45
3
2
004 , pp. 341–359.
(
t, J = 7.675 Hz, 2H), 7.55 (t, J = 7.30 Hz, 1H), 7.95(d, J = 7.78 Hz, 2H).
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3
3
C NMR: (CDCl , 100 MHz): d = 26.5, 128.2, 128.5, 133.1, 137.2,
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98.1.
8
81–888.
Benzophenone (Table 1, entry 10): White solid, mp 47–48 8C;
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IR (KBr): 3643, 3055, 1982, 1650, 1276 cm ; H NMR: (400 MHz,
CDCl ): = 7.48 (t, J = 7.37 Hz, 4H,), 7.58 (t, J = 7.22 Hz, 2H), 7.80 (d,
J = 7.75 Hz, 4H). C NMR: (CDCl
893–898.
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3
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32.4, 137.5, 196.7.
Cinnamaldehyde (Table 1, entry 11): Oil; IR (KBr): 2816, 2743,
À1
1
1
676 cm
;
H NMR (CDCl
3
, 400 MHz):
d
= 6.73 (dd, J = 16.1 Hz,
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(m, 2H), 9.72 (d, J = 7.8 Hz, 1H); C NMR (CDCl
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1
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Acknowledgment
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4052–4060.
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This research is supported by the Islamic Azad University,
Ayatollah Amoli Branch.
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