Methanol → Undecylenyl Iodide Eicosene

HRID 373756

Reaction equation

HRID 373756 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>C1(C)C=CC=CC=1>[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

6

Reactant 4

HCID 887MethanolHCID 189361-EicoseneHCID 1111946211-Iodoundec-1-eneHCID 16686102Diethyl aluminum chloride

Product 1

HCID 131717650Undecylenyl Iodide EicoseneYield 62.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a glass screw top jar were added undecylenyl iodide (5 grams), toluene solvent (30 grams) and eicosene (5 grams, Aldrich Chemical). Under argon atmosphere were added diethyl aluminum chloride (10 milliliters of a 1.8 molar solution in toluene) and 0.5 teaspoon of TiCl3 --AA (available from Alfa, about 2 grams). Two additional charges of both catalysts were added in 90 minute intervals and then the reaction mixture was stirred for 16 hours at 25° C. Methanol was added and the mixture was precipitated into methanol/hydrochloric acid using a Waring blender. The solids were sequentially washed with methanol, water and then methanol using a blender and the residue was isolated by filtration and dried in vacuo to yield 6.26 grams of the grey rubbery product, poly(undecylenyl iodide-eicosene) copolymer. 13C NMR (in deuterated chloroform) analysis measured a ratio of CH2 --I groups to CH3 groups present to be 31 weight percent.

Workup

  1. additionTwo additional charges of both catalysts were added in 90 minute intervals
  2. customthe mixture was precipitated into methanol/hydrochloric acid using a Waring blender
  3. washThe solids were sequentially washed with methanol, water
  4. custommethanol using a blender and the residue was isolated by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-73ac98c1423d472d898afb85def600b8
Source dataset
uspto-grants-1992_11
Patent number
US05166026

Linked notes

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