HCID 178447831, compound → HCID 178448008, compound

HRID 1632710Notes

Reaction equation

HRID 1632710 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]2[CH2:15][CH2:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH2:27][CH2:26][CH:25]([C@H:28]5[CH2:33][CH2:32][C@H:31]([CH2:34][CH2:35][CH3:36])[CH2:30][CH2:29]5)[CH2:24][CH:23]=4)=[CH:18][CH:17]=3)=[CH:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]>[Ni].C1(C)C=CC=CC=1>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C@H:7]([C@H:10]2[CH2:11][CH2:12][C@H:13]([C:16]3[CH:21]=[CH:20][C:19]([C@H:22]4[CH2:27][CH2:26][C@H:25]([C@H:28]5[CH2:29][CH2:30][C@H:31]([CH2:34][CH2:35][CH3:36])[CH2:32][CH2:33]5)[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[CH2:14][CH2:15]2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 178447831HCID 178447831, compound

Product 1

HCID 178448008HCID 178448008, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1140TolueneSolvent

Procedure

Raney Ni catalyst (0.5 g) was added to a solution of 1,4-bis[4-(trans-4-propylcyclohexyl)cyclohexen-1-yl]benzene (0.9 g) dissolved in toluene (70 ml), followed by subjecting to catalytic reduction at ordinary temperature under ordinary pressure, tracing the reaction by gas chromatography and stopping the reaction when the raw material disappeared. Since the product was a mixture of cis-form and trans-form substances, it was recrystallized from toluene to obtain an objective product, 1,4-bis[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene (yield: 0.3 g, C-Sm point: room temperature or lower, Sm-I point: 300° C. or higher).

Workup

  1. customthe reaction by gas chromatography
  2. additiona mixture of cis-form and trans-form substances, it
  3. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-41f17230653e49b2bfbc5240f73e346f
Source dataset
uspto-grants-1984_10
Patent number
US04477369

Reaction notes

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