Dodec-3-yn-1-ol → 3-Dodecen-1-ol, (3Z)-

HRID 1388879Notes

Reaction equation

HRID 1388879 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]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(OCC)(=O)C>[CH2:1]([OH:13])[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

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

Product 1

HCID 53646263-Dodecen-1-ol, (3Z)-Yield 91.6%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.20 g (17.5 mmoles) of 3-dodecyn-1-ol in 35 ml. of ethyl acetate was added 0.300 g of Lindlar catalyst (Lindlar, Helvetica Chimica Acta 35, 450 (1952)). The hydrogenation was carried out at atmospheric pressure with stirring. When the theoretical quantity of hydrogen had been taken up, the hydrogenation was stopped and the reaction mixture was filtered through Celite. After removal of the solvent, in vacuo, the residue was evaporatively distilled under reduced pressure to afford 2.95 g (91.6%) of (Z)-3-dodecen-1-ol as an oil.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. customAfter removal of the solvent
  3. distillationin vacuo, the residue was evaporatively distilled under reduced pressure

Sources & evidence

ORD record
ord-de7720d0f0d840a1bc1fb8d8b5d540fd
Source dataset
uspto-grants-1984_02
Patent number
US04434101

Reaction notes

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