Sodium Iodide → 3,3-Diphenylpropyl iodide

HRID 2228666Notes

Reaction equation

HRID 2228666 reaction equation
[I-:1].[Na+].CS(O[CH2:8][CH2:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)=O>CC(C)=O>[C:11]1([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][CH2:8][I:1])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 222382923,3-Diphenylpropyl methanesulfonate

Product 1

HCID 155128783,3-Diphenylpropyl iodideYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of sodium iodide (2.80 g, 18.9 mmol) in acetone (20 mL) was added a solution of 3,3-diphenylpropyl methanesulfonate (5.00 g, 17.2 mmol) in acetone (10 mL) at 0° C. and the mixture was refluxed for 3 hours. After cooling, the solvent was distilled off under reduced pressure and the residue was diluted with water (30 mL) and extracted with 2 portions of ethyl acetate. The pooled extract was washed with saturated aqueous sodium chloride solution, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was crystallized from methanol to provide 4.70 g of the title compound. Yield 85%.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionthe residue was diluted with water (30 mL)
  5. extractionextracted with 2 portions of ethyl acetate
  6. extractionThe pooled extract
  7. washwas washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-563840d8e75b4439b1542d1c4a9959ff
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

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