Acetylene → 3-Dodecen-1-ol, (3Z)-

HRID 462389Notes

Reaction equation

HRID 462389 reaction equation
[CH2:1]([OH:13])[CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H][H].C#C>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH3:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]/[CH:4]=[CH:3]\[CH2:2][CH2:1][OH:13]

Participants

6

Reactant 3

HCID 6326AcetyleneHCID 4108965Dodec-3-yn-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 53646263-Dodecen-1-ol, (3Z)-Yield 95.2%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 24 g of 3-dodecyn-1-ol in 400 ml of ethanol and 1 g of Lindlar catalyst was hydrogenated under 1 atmosphere of hydrogen. The progress of the reaction was followed by gas chromatography until the acetylene was consumed. The catalyst was removed by filtration through celite and the ethanol evaporated. The resulting residue was distilled to give 23.09 g of 3Z-dodecen-1-ol, bp 83-86/0.3 mm.

Workup

  1. customwas consumed
  2. customThe catalyst was removed by filtration through celite
  3. customthe ethanol evaporated
  4. distillationThe resulting residue was distilled

Sources & evidence

ORD record
ord-fc9da7649be44d6c97d3323763de38ce
Source dataset
uspto-grants-1985_05
Patent number
US04515727

Reaction notes

Loading…