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

HRID 1462610Notes

Reaction equation

HRID 1462610 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][CH:14]2[CH2:19][CH2:18][CH:17]([C:20]#[N:21])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][CH:17]([C:20]#[N:21])[CH2:18][CH2:19]2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 542178694-[2-(p-Pentylphenyl)ethenyl]cyclohexanecarbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 212853324-[2-(p-Pentylphenyl)ethyl]cyclohexanecarbonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

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.

Workup

  1. customcame to a standstill (about 30 minutes)
  2. filtrationFiltration 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

Sources & evidence

ORD record
ord-9b7ff9f91173481db4c89cdb1aceefb4
Source dataset
uspto-grants-1984_07
Patent number
US04460770

Reaction notes

Loading…