Rapid Dehydration of Aldoximes to Nitriles
113
than 4 min, benzonitrile was obtained almost quantitatively. To assess the general-
ity of the method, a variety of aldoximes were converted to the corresponding nitriles
in very short reaction times and high yields under the same conditions (Table 1).
In conclusion, we have developed a mild, ef®cient, inexpensive, and rapid
method for the direct conversion of aldoximes to nitriles.
Experimental
All products are known compounds; their physical data agreed with those of authentic samples.
General procedure
3
mmol of an appropriate oxime 1 and 5.05 mmol phthalic anhydride were added to 10 cm of
5
anhydrous acetonitrile. The resulting mixture was immediately placed into a microwave oven operat-
ing at medium to high power for the time indicated (Table 1). Then, the solvent was evaporated, and
3
the resulting residue was extracted with 3 Â 30 cm of CH Cl . The organic layer was washed with
2
2
5
% NH and an excess of H O to remove phthalic acid. The organic layer was dried over MgSO and
3 2 4
then evaporated. The residue was recrystallized from n-hexane/ethylacetate (Table 1, entries 2, 4±7,
9
, 10) or puri®ed by passing through a short silicagel column using CHCl as eluent (Table 1, entries
3
1
, 3, 8) to give pure nitrile 2.
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