1786
B. Akhlaghinia
synthesized as described in the literature.13 The products were puri-
fied by column chromatography, and the purity determination of the
products was accomplished by GLC on a Shimadzu model GC 10-A
instrument using n-octane as internal standard or by thin layer chro-
matography on silica gel polygram on SIL G/UV 254 plates. NMR spec-
tra were recorded on a Bruker Advance DPX 250 MHz instrument.
Typical Procedure for Conversion of Benzyl
Tetrahydropyranyl Ether to Benzyl Cyanide
To a flask containing a mixture of DDQ (2 mmol, 0.454 g) and Ph3P
(2 mmol, 0.524 g) in dry CH3CN (5 ml), while stirring Bu4NCN (2 mmol,
0.537 g) was added. Benzyl tetrahydropyranyl ether (1 mmol, 0.192 g)
was then added to this mixture. The reaction mixture was refluxed. GC
analysis showed that the reaction was completed after 4 h. The solvent
was evaporated under reduced pressure. Column chromatography of
the crude product on silica gel using n-hexane as eluent gave benzyl
cyanide in 96% yield. The product was identified by comparison of its
physical constants and spectral data with those of an authentic sample.
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