Phenol → HCID 178444518, compound

HRID 1154080Notes

Reaction equation

HRID 1154080 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(O)C=CC=CC=1.[H][H]>[Ni].C(O)C>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 996Phenol2×HCID 178418361HCID 178418361, compoundHCID 178444358HCID 178444358, compound

Product 1

HCID 178444518HCID 178444518, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Ten % by weight (20 g) of Raney nickel was added to 4-(trans-4'-pentylcyclohexyl)phenol (200 g), and ethanol (1.8 l) was added to dissolve the phenol, followed by absorbing 3 mols of hydrogen based on one mol of the raw material phenol, into the solution at 100° C. under a hydrogen pressure of 20 Kg/cm2G. After completion of the hydrogenation, the catalyst was filtered off and ethanol was vaporized to concentrate the solution so as to give a volume of about 0.3 l, followed by adding fresh ethanol, recrystallization and filtration to obtain trans-4-(trans-4'-pentylcyclohexyl)cyclohexanol (77 g) (yield: 37.6%).

Workup

  1. additionwas added
  2. filtrationAfter completion of the hydrogenation, the catalyst was filtered off
  3. concentrationto concentrate the solution so as
  4. customto give a volume of about 0.3 l
  5. additionby adding fresh
  6. customethanol, recrystallization and filtration

Sources & evidence

ORD record
ord-1d39b8f368864b6ebeac96a66595a21a
Source dataset
uspto-grants-1984_12
Patent number
US04487954

Reaction notes

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