p-[4-[2-(p-Pentylphenyl)vinyl]cyclohexyl]benzonitrile → HCID 178442124, compound

HRID 1249306Notes

Reaction equation

HRID 1249306 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]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)[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:11]=[CH:10][C:9]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]3[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 54279685p-[4-[2-(p-Pentylphenyl)vinyl]cyclohexyl]benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 178442124HCID 178442124, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

7.0 g of p-[4-[2-(p-pentylphenyl)vinyl]cyclohexyl]benzonitrile were dissolved in 350 ml of toluene, treated with 1.4 g of palladium/carbon (10%) and hydrogenated at room temperature and normal pressure until the hydrogen uptake came to a standstill. The crude p-[trans-4-[2-(p-pentylphenyl)ethyl]cyclohexyl]benzonitrile obtained after filtering off the catalyst and concentrating the filtrate was recrystallized twice from ethanol. Yield 4.2 g; m.p. (C--N) 61.5° C., cl.p. (N--I) 126° C.

Sources & evidence

ORD record
ord-eaf32b55cce146ad96514da54c35bb6b
Source dataset
uspto-grants-1986_12
Patent number
US04630896

Reaction notes

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