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

HRID 2214314Notes

Reaction equation

HRID 2214314 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-5fd83a10d4d941dbb8fe837ed91a53a3
Source dataset
uspto-grants-2006_09
Patent number
US07108033B2

Reaction notes

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