Phenylisohexanol → 3-Methyl-5-cyclohexylpentanol

HRID 565190Notes

Reaction equation

HRID 565190 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:4][OH:5]>[Ni].O>[CH3:1][CH:2]([CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH2:3][CH2:4][OH:5]

Participants

4

Reactant 1

HCID 108312Phenylisohexanol

Product 1

HCID 212677663-Methyl-5-cyclohexylpentanolYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent2×

Procedure

3-Methyl-5-phenylpentanol (50 g., 0.28 mol.) and 1 g. of 50% Ni on silica catalyst (2 wt %, G-49-C, United Catalyst) were stirred at 700 rpm in a Parr reactor at 180° C. and 200-600 psi of hydrogen until hydrogen absorption stopped (12 hours). The reaction mixture was filtered through a filter bed (Celite™) using toluene as a rinse solvent and concentrated to a clear, colorless liquid. The odor grade product was isolated by fractional distillation, 96% yield; bp 84-86° C. at 0.8 mm. Odor: powerful green, rosy. Mass Spectrum form 5313-24. MS (EI) m/z (relative intensity) 166 (M+−H2O, 5), 151 (M+−Me and H2O, 2).

Workup

  1. custom200-600 psi of hydrogen until hydrogen absorption
  2. custom(12 hours)
  3. filtrationThe reaction mixture was filtered through a filter bed (Celite™)
  4. concentrationconcentrated to a clear, colorless liquid
  5. customThe odor grade product was isolated by fractional distillation, 96% yield

Sources & evidence

ORD record
ord-3b98f67de59f471ab83048413f14091d
Source dataset
uspto-grants-2001_01
Patent number
US06172016B2

Reaction notes

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