6-Cyclohexylidene-hexan-1-ol → 6-Cyclohexanehexanol

HRID 9811Notes

Reaction equation

HRID 9811 reaction equation
[C:1]1(=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd]>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 140222306-Cyclohexylidene-hexan-1-ol

Product 1

HCID 203646-CyclohexanehexanolYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 6-cyclohexylidene-hexan-1-ol (1.05 g, 5.77 mmol) in MEOH (40 mL) was hydrogenated with Pd—C (0.23 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 6-cyclohexyl-hexan-1-ol (1.02 g, 96%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.63 (2H, t, J=6.6 Hz), 1.46–1.80 (7H, m), 1.04–1.44 (12H, m), 0.86 (2H, m); 13C NMR (75 MHz, CDCl3) δ 63.33, 37.92, 37.74, 33.72, 33.08, 30.04, 27.10, 27.04, 26.73, 26.05.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5ad26e7da6b343a29d1920b184022d66
Source dataset
uspto-grants-2006_08
Patent number
US07091357B2

Reaction notes

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