4-[2-(p-Pentylphenyl)ethenyl]cyclohexanecarbonitrile → 4-[2-(p-Pentylphenyl)ethyl]cyclohexanecarbonitrile
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
Procedure
956 mg of the 4-[2-(p-pentylphenyl)ethenyl]cyclohexanecarbonitrile obtained were dissolved in 50 ml of toluene in a sulphonation flask, treated with 150 mg of 10% palladium/carbon and hydrogenated at normal pressure and room temperature until the hydrogen uptake came to a standstill (about 30 minutes). Filtration of the mixture (rinsing with toluene), concentration of the filtrate and low-pressure chromatography (0.4 bar) of the residue (890 mg) on silica gel using 5% ethyl acetate/petroleum ether as the eluting agent gave 788 mg (82%) of 4-[2-(p-pentylphenyl)ethyl]cyclohexanecarbonitrile (cis/trans ratio about 1:3 according to gas chromatography and NMR spectroscopy). Two-fold crystallization from pentane at -20° C. finally yielded the trans-nitrile (trans content 98.8%); m.p. (C-I) 22.4° C., cl.p. (N-I) -14.1° C., Rf value (5% ethyl acetate/petroleum ether) 0.22.
Workup
- customcame to a standstill (about 30 minutes)
- filtrationFiltration of the mixture (rinsing with toluene), concentration of the filtrate and low-pressure chromatography (0.4 bar) of the residue (890 mg) on silica gel using 5% ethyl acetate/petroleum ether as the eluting agent
Sources & evidence
- ORD record
- ord-b7ee66b85c864a38ae4440680022f30f
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04526704
Reaction notes
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