Tetrahedron p. 5699 - 5702 (2008)
Update date:2022-08-11
Topics:
Kamitanaka, Takashi
Yamamoto, Kenji
Matsuda, Tomoko
Harada, Tadao
The reactions of benzonitrile in supercritical methanol, ethanol, and 2-propanol were investigated under non-catalytic conditions. In supercritical methanol, benzonitrile was converted to methyl benzoate in high yield. The esterification reaction also occurred in supercritical ethanol to afford ethyl benzoate in moderate yield. The esterification could occur via a route analogous to the Pinner reaction. On the other hand, benzonitrile in supercritical 2-propanol yielded no ester. Benzyl alcohol was the major product in supercritical 2-propanol. We investigated the reaction of the C{double bond, long}N bond in supercritical 2-propanol. In supercritical 2-propanol, N-benzylideneaniline was transferred to the reduction product (N-benzylaniline) and hydrolysis products (benzyl alcohol and aniline). The hydrolysis reaction was restricted when the reaction was carried out in supercritical 2-propanol with a low water content. This indicates that the water in the 2-propanol acts as a reagent for the hydrolysis of the C{double bond, long}N bond. These results suggested the following reaction process: C6H5C{triple bond, long}N→C6H5CH{double bond, long}NH→C6H5CHO→C6H5CH2OH.
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