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 27673

Reaction equation

HRID 27673 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-c7b9c1f3bf1840198edcbddc3c0525c9
Source dataset
uspto-grants-1980_09
Patent number
US04222963

Linked notes

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