4-Isopropenyl-3,7-dimethyl-6-octen-1-yn-3-ol → 3,7-Dimethyl-4-(prop-1-en-2-yl)octa-1,6-dien-3-ol

HRID 1448195Notes

Reaction equation

HRID 1448195 reaction equation
[C:1]([CH:4]([CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[C:5]([CH3:9])([OH:8])[C:6]#[CH:7])([CH3:3])=[CH2:2]>CCCCCC.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[C:1]([CH:4]([CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[C:5]([CH3:9])([OH:8])[CH:6]=[CH2:7])([CH3:3])=[CH2:2]

Participants

4

Reactant 1

HCID 135824294-Isopropenyl-3,7-dimethyl-6-octen-1-yn-3-ol

Product 1

HCID 124529723,7-Dimethyl-4-(prop-1-en-2-yl)octa-1,6-dien-3-olYield 95.4%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8058HexaneSolvent

Procedure

A solution of 500 g of 4-isopropenyl-3,7-dimethyl-6-octen-1-yn-3-ol in 1.5 liters of n-hexane was hydrogenated at ambient temperature and atmospheric pressure using 25 g of 0.25% Lindlar catalyst. The reaction was sequentially monitored by gas chromatography (PEG20M, 150° C.) and the reaction was terminated when no starting material remained. The catalyst was filtered off and the solvent was removed from the filtrate by distillation under reduced pressure. The residue was distilled in vacuo to obtain 482 g of 4-isopropenyl-3,7-dimethyl-1,6-octadien-3-ol as a fore-running distillate at bp. 55°-59° C./0.4 mm Hg.

Workup

  1. customwas hydrogenated at ambient temperature
  2. customwas sequentially monitored by gas chromatography (PEG20M, 150° C.)
  3. customthe reaction was terminated when no starting material
  4. filtrationThe catalyst was filtered off
  5. customthe solvent was removed from the filtrate by distillation under reduced pressure
  6. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-e44530db800d41899ca8fde913109e70
Source dataset
uspto-grants-1979_12
Patent number
US04179579

Reaction notes

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