4-(Trifluoromethyl)phenol → 4-(Trifluoromethyl)cyclohexan-1-ol

HRID 1361289Notes

Reaction equation

HRID 1361289 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[H][H]>C(O)(=O)C>[F:9][C:8]([F:10])([F:11])[CH:5]1[CH2:4][CH2:3][CH:2]([OH:1])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 678744-(Trifluoromethyl)phenolHCID 178418361HCID 178418361, compound3×

Product 1

HCID 27797654-(Trifluoromethyl)cyclohexan-1-olYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Hydroxybenzotrifluoride (5 g, 30.8 mmol) was placed in a hydrogen reaction vessel, dissolved in acetic acid (15 ml), and Pt−2O (500 mg) was added. The hydrogen reaction vessel was pressurized with hydrogen (50 psi), and reacted for 16 h. After the reaction finished, the reaction mixture was filtered through Celite, and to the filtrate was added 1N-NaOH, extracted with diethylether, dried over MgSO4, and concentrated in vacuo at rt to give the title compound (4.5 g, 87%).

Workup

  1. customreacted for 16 h
  2. filtrationthe reaction mixture was filtered through Celite
  3. additionto the filtrate was added 1N-NaOH
  4. extractionextracted with diethylether
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo at rt

Sources & evidence

ORD record
ord-2ade2c5250d34b5d8214a34a6e065be1
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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