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

HRID 1261868Notes

Reaction equation

HRID 1261868 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].[H][H]>[Ni].C(O)C>[CH3:5][CH:4]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:10])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:3][CH2:2][OH:1]

Participants

5

Reactant 2

HCID 3327a FarnesolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 1388243,7,11-Trimethyl-1-dodecanolYield 88%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

Under nitrogen in a 1 liter 3-neck flask equipped with mechanical stirring, Raney Nickel (Raney 2800, Aldrich, 30% slurry in water, 20.4 g) was suspended in ethanol (400 mL). A solution of farnesol (mixture of cis and trans isomers, 25.0 g), in ethanol (75 mL) was added dropwise with a gentle sweep of hydrogen through the reaction mixture, and the mixture was stirred under hydrogen for 144 hours. Hydrogen was then replaced by nitrogen, and under a positive pressure of nitrogen the suspension was filtered through a filter stick. The catalyst was suspended in a small volume of ethanol and the filtration was repeated. Finally the catalyst was suspended in water and the suspension was rejected. The ethanol filtrate was filtered again through celite and the filtrate was concentrated. After extractive work-up using toluene, the residue was distilled under vacuum. The desired product, by 112-115° C., was obtained as a colorless liquid, 22.76 g (88% yield). Mass spec: m/z 226 (M−2)+. Anal. Calcd for C15H32O: C, 78.88%; H, 14.12%. Found: C, 77.90%; H, 14.32%. No hydrocarbon was detected in the fore-run (0.28 g) or distillation residue (0.9 g). The alcohol product was converted to the corresponding bromide, without additional purification.

Workup

  1. filtrationunder a positive pressure of nitrogen the suspension was filtered through a filter stick
  2. filtrationthe filtration
  3. filtrationThe ethanol filtrate was filtered again through celite
  4. concentrationthe filtrate was concentrated
  5. distillationthe residue was distilled under vacuum

Sources & evidence

ORD record
ord-3aa39a98d2d947e198191a61268c34ae
Source dataset
uspto-grants-2013_06
Patent number
US08471035B1

Reaction notes

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