5-Phenyl-1-pentanol → Cyclohexanepentanol

HRID 654896Notes

Reaction equation

HRID 654896 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)(=O)C.C(OCC)C.[Pt]=O>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 615235-Phenyl-1-pentanolHCID 178418361HCID 178418361, compound

Product 1

HCID 269450Cyclohexanepentanol

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-phenylpentanol (2.21 g., 13.5 mmol) in ten ml glacial acetic acid was added amorphous platinum oxide (0.40 g., 1.76 mmol, oxygen activated). This mixture was subjected to three atm. of hydrogen with agitation (Parr hydrogenator) at room temperature for four hours. The reaction mixture was diluted with ethyl ether, filtered through celite, washed repeatedly with saturated sodium bicarbonate, followed by water and saturated sodium chloride solution. The organic portion was filtered, dried over magnesium sulfate, filtered and concentrated to give the desired alcohol.

Workup

  1. filtrationfiltered through celite
  2. washwashed repeatedly with saturated sodium bicarbonate
  3. filtrationThe organic portion was filtered
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ecf8f125a674a57bc18840d689fdf3f
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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