Sodium Iodide → 1-Ethenyl-4-(iodomethyl)benzene

HRID 1744994Notes

Reaction equation

HRID 1744994 reaction equation
[I-:1].[Na+].[CH:3]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Cl)=[CH:7][CH:6]=1)=[CH2:4]>CC(C)=O>[CH:3]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][I:1])=[CH:7][CH:6]=1)=[CH2:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 219463111-Ethenyl-4-(iodomethyl)benzeneYield 84.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (1.2 equiv., 59 g, 0.39 mol) was dissolved in acetone (200 ml) and 4-vinylbenzyl chloride (50 g, 0.33 mol) was added to a reaction flask. The mixture was stirred at room temperature overnight. The reaction mixture was filtered and acetone removed under reduced pressure. The resulting product was dissolved in hexane, filtered, and the solvent removed under reduced pressure. The monomer was isolated as a red, slightly viscous liquid (68 g, yield 84%). 1H NMR (CDCl3) δ (ppm) 4.47 (s, 2H), 5.25 (d, 1H), 5.74 (d, 1H), 6.65 (dd, 1H), 7.34 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customacetone removed under reduced pressure
  3. dissolutionThe resulting product was dissolved in hexane
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0aa956d0aba04a929f7dcc2e87d8034a
Source dataset
uspto-grants-2006_03
Patent number
US07019096B2

Reaction notes

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