Tricyclohexylphosphine → 1,4,6-Octatriene, 2,7-dimethyl-, (E)-

HRID 918225Notes

Reaction equation

HRID 918225 reaction equation
[CH3:1][C:2]([CH3:10])=[CH:3][CH:4]=[CH:5][CH2:6][CH2:7][CH:8]=C.[CH:11]1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2]>[CH3:11][C:7]([CH2:6][CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[CH3:10])=[CH2:8]

Participants

4

Reactant 2

HCID 75806TricyclohexylphosphineHCID 54211005Dimethyl-octa-1,3,7-triene

Product 1

HCID 5280381,4,6-Octatriene, 2,7-dimethyl-, (E)-Yield 80.3%

Reagents, catalysts & solvents 1

HCID 5486778Palladium acetylacetonateCatalyst

Procedure

10 g of dimethyl-1,3,7-octatriene are kept under argon atmosphere for 36 hours with 0,303 g palladium acetylacetonate, 1,4 g of tricyclohexylphosphine and 0,1 g of H3Po4. After this period, 80.3% of 2,7-dimethyl-1,4,6-octatriene have been formed (GC-analysis).

Workup

  1. waitAfter this period

Sources & evidence

ORD record
ord-a5aa6b04aa4d42d6b2d1bf80c7381fa9
Source dataset
uspto-grants-1976_07
Patent number
US03970592

Reaction notes

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