a Farnesol → 3,7,11-Trimethyl-1-dodecanol

HRID 1819548Notes

Reaction equation

HRID 1819548 reaction equation
[OH:1][CH2:2][CH:3]=[C:4]([CH2:6][CH2:7][CH:8]=[C:9]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:10])[CH3:5]>[Pd].C(O)C>[CH3:16][CH:14]([CH2:13][CH2:12][CH2:11][CH:9]([CH2:8][CH2:7][CH2:6][CH:4]([CH2:3][CH2:2][OH:1])[CH3:5])[CH3:10])[CH3:15]

Participants

4

Reactant 1

HCID 3327a Farnesol

Product 1

HCID 1388243,7,11-Trimethyl-1-dodecanolYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A flask containing a stirring suspension of farnesol (5.7 ml, 22.5 mmol) and palladium on carbon (10% Pd, 1 g, 0.04 equ) in ethanol (15 ml) was evacuated, and then filled with hydrogen. The reaction mixture was then stirred under an atmosphere of hydrogen for 36 hours. After this time the reaction was filtered and the filtrate concentrated in vacuo to give hexahydrofarnesol (44) (4.81 g, 93%) as a colourless oil.

Workup

  1. additionA flask containing
  2. customwas evacuated
  3. additionfilled with hydrogen
  4. filtrationAfter this time the reaction was filtered
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-b0ef7d186e944c089925464c426a9ee1
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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