Synthesis of Nitroalkanes
J. Chin. Chem. Soc., Vol. 52, No. 2, 2005 311
To 40 mL of a 3 M solution of sodium nitrite was added
[P4-Et] I and slowly stirred for 24 hr. The resin [P4-Et] NO2
was filtered off and washed rapidly with distilled water until
was filtered and washed with n-hexane and ether. The com-
bined filtrate was evaporated to obtain nitroethane. b.p =
110-114 °C, 1H NMR, d (ppm): 4.3 (q, 2H), 1.38 (t, 3H).
-
the filtrate gave a negative test for NO2 . It was then washed
with ether and dried under vacuum in the presence of P2O5 at
40 °C (1.6 g).
ACKNOWLEDGEMENT
The activity of these polymers was determined by
potentiometric titration with a 0.1N solution of silver nitrate.
The activity of polymer (1) was 4.8 mmol/g of the polymer,
and the activity of polymer (2) was 3.7 mmol/g of the poly-
mer.
The authors are thankful to Professor Bahman Tamami
and Dr. Bi Bi Fatemeh Mirjalili for helpful discussions.
Received June 23, 2004.
General procedure for conversion of alkylhalides to cor-
responding nitroalkanes
To a mixture of alkylhalide (1 mmol) and n-hexane (10
mL) in a round-bottomed flask (50 mL), 2 mmol of polymer
(1) or (2) was added, and the mixture stirred at room tempera-
ture for 17-72 hr (Table 1). The formation of nitro compounds
was monitored by TLC (eluent: chloroform) or GLC. On
completion of reaction, the mixture was filtered and washed
with n-hexane and ether. The combined filtrate was evapo-
rated to obtain nitroalkanes in 11-99% yield. The spent poly-
meric reagent was regenerated by treatment with sodium ni-
trite solution. The regenerated reagent has the same capacity
as the original form.
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polymer (2): A typical procedure
To a mixture of iodoethane (0.4 mL, 5 mmol) and n-
hexane (10 mL) in a round-bottomed flask (50 mL), 10 mmol
of polymer (2) (2.7 gr) was added, and the mixture stirred at
room temperature for 33 hr. The formation of product was
monitored by GLC. On completion of reaction, the mixture
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