Carbon Tetrachloride → (Z,Z)-1-chloro-2,5-undecadiene

Reaction equation

[CH:1](/O)=[CH:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC.C(Cl)(Cl)(Cl)[Cl:39]>>[Cl:39][CH2:1]/[CH:2]=[CH:3]\[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

Reactant 4

HCID 5943Carbon Tetrachloride

HCID 8058Hexane

HCID 11776Triphenylphosphine

HCID 86738537(Z,Z)-undecadien-1-ol

Product 1

HCID 13044960(Z,Z)-1-chloro-2,5-undecadieneYield 92%

Conditions

Temperature: 23 °C

Procedure

A mixture of (Z,Z)-undecadien-1-ol (3.42 g, 20.4 mmol) and triphenylphosphine (7.5 g, 28.6 mmol) in dry CCl4 (25 ml) was refluxed with stirring for 9 h. The reaction mixture was allowed to cool to 23° C., hexane (60 ml) was added, and stirring was continued for an additional 10 minutes. The precipitate of triphenylphosphine oxide was filtered and washed with hexane. The solvent was removed from the combined filtrate at 40° C./~ 30 mmHg. Evaporative distillation of the resulting residue at 125°-130° C./0.3 mmHg gave 3.5 g (92%) of (Z,Z)-1-chloro-2,5-undecadiene as a colorless liquid.