3-Octyn-1-ol → 3-Octen-1-ol, (3Z)-

HRID 1065948Notes

Reaction equation

HRID 1065948 reaction equation
[H][H].[CH2:3]([OH:11])[CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH3:10]>CCCCCC.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:3]([OH:11])[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 846943-Octyn-1-olHCID 178418361HCID 178418361, compound2×

Product 1

HCID 53645193-Octen-1-ol, (3Z)-

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8058HexaneSolvent

Procedure

The hydrogen reduction of this 3-octyn-1-ol is carried out by dissolving the compound in n-hexane with addition of 3 to 20% by weight of a Lindlar catalyst and introducing hydrogen at room temperature with agitation (reaction (iii)). Removal of the catalyst by filtration and n-hexane by distillation from the reaction mixture gives cis-3-octen-1-ol in an almost quantitative yield.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and n-hexane
  3. distillationby distillation from the reaction mixture

Sources & evidence

ORD record
ord-a2c654ff179d4d5aa4d1b5b7c0059193
Source dataset
uspto-grants-1982_05
Patent number
US04331820

Reaction notes

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