Sodium Iodide → 11-Iodoundec-1-ene

HRID 2399692Notes

Reaction equation

HRID 2399692 reaction equation
[CH2:1]([I:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[I-].[Na+].[CH2:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH3:16]>CC(C)=O.C(C(C)=O)C>[I-:12].[CH2:1]([N+:17]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:15][CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[CH2:1]([I:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

7

Reactant 3

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 1111946211-Iodoundec-1-ene

Product 2

HCID 1111946211-Iodoundec-1-eneHCID 85678669HCID 85678669, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Example IX involves the procedures followed above to prepare undecylenyl chloride, undecylenyl iodide, and triethylammonium undecylenyl iodide. All reagents were obtained from Aldrich unless specified otherwise. Undecylenyl iodide was made stepwise from undecylenol (Aldrich). Undecylenol was allowed to react with thionyl chloride and pyridine to form undecylenyl chloride which was then converted to undecylenyl iodide by reaction with sodium iodide in acetone or methyl ethyl ketone. Undecylenyl triethylammonium iodide was formed by the reaction of undecylenyl iodide and triethylamine in alcohol. Polyalkylenes were then made by polymerization of the corresponding 1-olefins using the isotactic catalyst TiCl3AA (Alpha Products)/diethylaluminum chloride.

Sources & evidence

ORD record
ord-c0404d1eac234d05a687d99a963bd688
Source dataset
uspto-grants-1995_09
Patent number
US05451483

Reaction notes

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