7-Methyl-oct-6-en-1-ol → Isononanol

HRID 9822

Reaction equation

HRID 9822 reaction equation
[CH3:1][C:2]([CH3:10])=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]>CO.[Pd]>[CH3:1][CH:2]([CH3:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]

Participants

4

Reactant 1

HCID 123068897-Methyl-oct-6-en-1-ol

Product 1

HCID 17072IsononanolYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7-methyl-oct-6-en-1-ol (1.42 g, 10.0 mmol) in MeOH (70 mL) was hydrogenated with Pd—C (0.40 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 7-methyl-octan-1-ol (1.38 g, 96%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.64 (2H, t, J=6.6 Hz), 1.54 (3H, m), 1.10–1.44 (8H, m), 0.88 (3H, s), 0.85 (3H, s); 13C NMR (75 MHz, CDCl3) δ 63.28, 39.21, 33.06, 29.98, 28.24, 27.64, 26.06, 22.94.

Workup

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

Sources & evidence

ORD record
ord-ed23eba753104b989acd5556d6c144e0
Source dataset
uspto-grants-2006_08
Patent number
US07091357B2

Linked notes

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