Reaction #2805

ord-e62ed52d8b364ce5b8047d942697fb19

Reaction equation

C=Cc1ccccc1CCl
1-chloromethyl-2-vinyl-benzene
[I-].[Na+]
sodium iodide
O
water
→
C=Cc1ccccc1CI
title compound
Yield 95.0%
C=Cc1ccccc1CI
1-Iodomethyl-2-vinyl-benzene
Yield 95.0%

Reactants

C=Cc1ccccc1CCl
1-chloromethyl-2-vinyl-benzene
[I-].[Na+]
sodium iodide
O
water

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureHeat
  2. 2
    Temperatureat gentle reflux for 30 minutes
  3. 3
    TemperatureCool
  4. 4
    Extractionextract with pentane (200 mL)
  5. 5
    DryingDry (MgSO4)
  6. 6
    Otherevaporate the solvent in vacuo

Procedure

Dissolve 1-chloromethyl-2-vinyl-benzene (4.0 g, 26 mmol) in acetone (100 mL) and add sodium iodide (4.5 g, 30 mmol). Heat at gentle reflux for 30 minutes. Cool, add water (150 mL) and extract with pentane (200 mL). Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound (95%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731306uspto-grants-1998_03