Sodium Iodide → 4-(Iodomethyl)benzyltri-n-butylammonium iodide

HRID 266005Notes

Reaction equation

HRID 266005 reaction equation
Cl[CH:2](Cl)[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[I-:11].[Na+].[CH2:13]([N:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16]>CC(C)=O>[I-:11].[I:11][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N+:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 7622TributylamineHCID 5200171-(Dichloromethyl)-4-methylbenzene

Product 1

HCID 190321734-(Iodomethyl)benzyltri-n-butylammonium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of α,α-dichloro-p-xylene (50 g, 28.6 mmol) and sodium iodide (8.6 g, 57 mmol) in acetone (100 mL) was added tri-n-butylamine (3.7 g, 20.0 mmol). The reaction mixture was stirred at room temperature under argon for several days after which time TLC examination showed completion of the reaction. The reaction mixture was filtered and the solvent was removed under reduced pressure to give an oily residue. The residue was washed with pentane several times and dried to give a yellow solid. The product was used without further purification.

Workup

  1. customcompletion of the reaction
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. customto give an oily residue
  5. washThe residue was washed with pentane several times
  6. customdried
  7. customto give a yellow solid
  8. customThe product was used without further purification

Sources & evidence

ORD record
ord-245940e0e64d49028a65aa7e6cbcb53c
Source dataset
uspto-grants-1997_07
Patent number
US05650099

Reaction notes

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