Methanol → 2,5-Undecadien-1-ol, (2Z,5Z)-

HRID 1463580Notes

Reaction equation

HRID 1463580 reaction equation
[CH3:1][OH:2].[CH2:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>[Pd]>[CH2:1]([OH:2])/[CH:8]=[CH:3]\[CH2:4]/[CH:5]=[CH:3]\[CH2:8][CH2:7][CH2:6][CH2:5][CH3:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 8078Cyclohexane

Product 1

HCID 117450382,5-Undecadien-1-ol, (2Z,5Z)-Yield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

6.2 G (37.8 mmole) of the carbinol obtained as indicated under letter i. above, dissolved in 50 ml of cyclohexane, were hydrogenated at atmospheric pressure in the presence of 120 mg of Lindlar type palladium catalyst. After filtration and evaporation, the obtained residue was chromatographed on a silica column, using as eluting agent a mixture of 1 to 10% ethyl acetate in cyclohexane, to give 5.9 g (yield: 95%) of undeca-2Z,5Z-dienol.

Workup

  1. filtrationAfter filtration and evaporation
  2. customthe obtained residue was chromatographed on a silica column
  3. washas eluting agent
  4. additiona mixture of 1 to 10% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-229acd8452ee4a1abbba2eefc2915cad
Source dataset
uspto-grants-1994_04
Patent number
US05300716

Reaction notes

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