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
5
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 mm Hg. Evaporative distillation of the resulting residue at 125°-130° C./0.3 mm Hg gave 3.5 g (92%) of (Z,Z)-1-chloro-2,5-undecadiene as a colorless liquid.
Workup
- temperaturewas refluxed
- stirringstirring
- waitwas continued for an additional 10 minutes
- filtrationThe precipitate of triphenylphosphine oxide was filtered
- washwashed with hexane
- customThe solvent was removed from the combined filtrate at 40° C./~30 mm Hg
- distillationEvaporative distillation of the resulting residue at 125°-130° C./0.3 mm Hg
Sources & evidence
- ORD record
- ord-5469bd2725b8466b9d62dfbaa632e0ff
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04642364
Reaction notes
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