4-[2-(p-Pentylphenyl)ethenyl]cyclohexanecarbonitrile → 4-[2-(p-Pentylphenyl)ethyl]cyclohexanecarbonitrile

Participants

Reaction Steps

956 mg of the 4-[2-(p-pentylphenyl)ethenyl]cyclohexanecarbonitrile obtained were dissolved in 50 ml of toluene in a sulphonation flask, the solution was treated with 150 mg of palladium/carbon (10%) and the mixture was hydrogenated at normal pressure and room temperature until the hydrogen uptake came to a standstill (about 30 minutes). Filtration of the mixture (back-washing with toluene), concentration of the filtrate and low-pressure chromatography (0.4 bar) of the residue (890 mg) on silica gel with 5% ethyl acetate/petroleum ether gave 788 mg (82%) of 4-[2-(p-pentylphenyl)ethyl]cyclohexanecarbonitrile as a viscous, colourless oil. Although in the thin-layer chromatogram using different solvent systems as the eluant there appeared only a single spot, with gas-chromatographic analysis and NMR spectroscopic analysis showed this material to be a cis/trans isomer mixture (about 1:3). Two-fold crystallization of this material from pentane at -20° C. finally yielded trans-4-[2-(p-pentylphenyl)ethyl]cyclohexanecarbonitrile of sufficient purity (98.8% of trans compound and 1.2% of cis compound according to gas-chromatographic analysis); m.p. 22.4° C.; cl.p. (N-I) -14.1° C.

Provenance & Evidence