(4-Pentyl-1-cyclohexenyl)-3,5-difluorobenzene → (4-Pentyl-cyclohexyl)-3,5-difluorobenzene

HRID 566158Notes

Reaction equation

HRID 566158 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)=[CH:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>[Ni].[C].[Pd]>[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:13]=[C:14]([F:19])[CH:15]=[C:16]([F:18])[CH:17]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 21265324(4-Pentyl-1-cyclohexenyl)-3,5-difluorobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 22242488(4-Pentyl-cyclohexyl)-3,5-difluorobenzeneYield 91%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 178418390HCID 178418390, compoundCatalyst

Procedure

Mixture of (4-pentyl-1-cyclohexenyl)-3,5-difluorobenzene (89 mmol), Raney nickel (3.5 g), and 500 ml of Solmix was subjected to a hydrogenation reaction at room temperature under normal pressure for 10 hours. At the time when the amount of hydrogen has come not to further reduce and the reaction has come not to progress, catalyst was changed from Raney nickel to palladium carbon (2.4 g), and stirred for 8 hours. Palladium carbon was filtered off and the solvent was distilled off. The residue was purified by column chromatography (eluent: heptane) to give a (4-pentyl-cyclohexyl)-3,5-difluorobenzene (81 mmol).

Workup

  1. customwas subjected to a hydrogenation reaction at room temperature under normal pressure for 10 hours
  2. filtrationPalladium carbon was filtered off
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by column chromatography (eluent: heptane)

Sources & evidence

ORD record
ord-d79e2e89be8f4e63859aa237b0ae9ac1
Source dataset
uspto-grants-2001_01
Patent number
US06174458B1

Reaction notes

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