1-Eicosene → Undecylenyl Iodide Eicosene

HRID 373755

Reaction equation

HRID 373755 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].[CH2:13]=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[Cl-].C([Al+]CC)C.CO.Cl>C1(C)C=CC=CC=1.CO>[CH2:1]([I:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[CH2:13]=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 189361-EicoseneHCID 1111946211-Iodoundec-1-eneHCID 16686102Diethyl aluminum chlorideHCID 21893726Hydrochloride methanol

Product 1

HCID 131717650Undecylenyl Iodide EicoseneYield 166.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

To a glass screw top jar were added undecylenyl iodide (6.3 grams), toluene solvent (63.1 grams), and eicosene (18.73 grams). Under argon atmosphere were added diethyl aluminum chloride (25 milliliters of a 1.8 molar solution in toluene) and 1.25 teaspoons of TiCl3 --AA (available from Alfa, about 5 grams). The sealed jar was stirred for 2 hours. Methanol was added dropwise until the mixture turned green. The reaction mixture was then added to methanol/hydrochloric acid in a Waring blender to precipitate the solid polymer. In the blender, the polymer was washed successively with methanol, water and then methanol. After filtration, the isolated polymer was dried in vacuo to yield 21.04 grams of the semicrystalline polymer product, poly(undecylenyl iodide-eicosene) copolymer, the DSC of this product indicated two semicrystalline endotherms at 30° and 55° C. Solid state 13C NMR analysis measured 17 weight percent of CH2 --I groups present.

Workup

  1. customto precipitate the solid polymer
  2. washIn the blender, the polymer was washed successively with methanol, water
  3. filtrationAfter filtration
  4. customthe isolated polymer was dried in vacuo

Sources & evidence

ORD record
ord-131e292e81bd46ebbb84c6b2b725a088
Source dataset
uspto-grants-1992_11
Patent number
US05166026

Linked notes

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