HCID 178455751, compound → HCID 178455763, compound

HRID 1632708Notes

Reaction equation

HRID 1632708 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([C@H:20]4[CH2:25][CH2:24][C@H:23]([CH2:26][CH3:27])[CH2:22][CH2:21]4)[CH2:16][CH2:15]3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[Ni]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([C@H:20]4[CH2:25][CH2:24][C@H:23]([CH2:26][CH3:27])[CH2:22][CH2:21]4)[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178455751HCID 178455751, compound

Product 1

HCID 178455763HCID 178455763, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1140TolueneSolvent

Procedure

4-Methyl-{4-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]cyclohexen-1-yl}benzene (3.2 g) was dissolved in toluene (300 ml) and Raney Ni catalyst (1.5 g) was added, followed by catalytic reduction under ordinary pressure at ordinary temperature. When the raw material disappeared through gas chromatography, the reaction finished. The solvent was distilled off and recrystallization from toluene was repeated to obtain 4-methyl-{trans-4-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]cyclohexyl}benzene (yield: 0.8 g) having a C-Sm point of 71.0° C., a Sm-N point of 254° C. and a N-I point of 293° C.

Workup

  1. distillationThe solvent was distilled off
  2. customrecrystallization from toluene

Sources & evidence

ORD record
ord-a991def696a6418bbd99894061877280
Source dataset
uspto-grants-1984_10
Patent number
US04477369

Reaction notes

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