Collect. Czech. Chem. Commun.
1987, 52, 1015-1020
https://doi.org/10.1135/cccc19871015
Hydrogenation of cinnamyl methyl ether and allylbenzene on palladium catalysts
Libor Červenýa, Ivo Pasekab, Eva Fialováa and Vlastimil Růžičkaa
a Department of Organic Technology, Prague Institute of Chemical Technology, 166 28 Prague 6
b Institute of Inorganic Chemistry, Czechoslovak Academy of Sciences, 160 00 Prague 6
Abstract
The hydrogenation of cinnamyl methyl ether and allylbenzene in hexane and acetone at 20 °C and atmospheric pressure of hydrogen has been studied on eight palladium catalysts. The hydrogenation of cinnamyl methyl ether is accompanied by C-O bond splitting giving rise to propylbenzene and methanol, the hydrogenation of allylbenzene is associated with the isomerization of the double bond resulting in its conjugation with the benzene ring. A marked solvent effect on the selectivity of hydrogenation of cinnamyl methyl ether has been observed and ascribed to the effect of solvated protons on the adsorbed molecules of the ether which is promoted by polar medium. The solvent effect on the isomerization of allylbenzene during the hydrogenation is little pronounced, which suggests that this reaction is not of ionic nature.
