Sodium Iodide → 3-Methoxyphenethyl iodide

HRID 568780Notes

Reaction equation

HRID 568780 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)(=O)=O.[I-:16].[Na+]>CC(C)=O>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][CH2:6][I:16]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 130615423-Methoxyphenethyl mesylate

Product 1

HCID 109014123-Methoxyphenethyl iodideYield 87.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a flask under argon was added 14.6 g (0.0634 mole) 2-(3-methoxyphenyl)ethyl methanesulfonate in 400 ml of acetone and 36.5 g (0.243 mole) of sodium iodide. The reaction mixture was refluxed for 2.5 hr. The acetone was evaporated in vacuo and the residue dissolved in ether. The ether was washed with water, sodium bicarbonate, sodium thiosulfate, water and brine, dried over MgSO4, and evaporated in vacuo to give a light green oil. Distillation in a Kugelrohr apparatus gave 14.6 g of the desired product as a clear oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hr
  2. customThe acetone was evaporated in vacuo
  3. dissolutionthe residue dissolved in ether
  4. washThe ether was washed with water, sodium bicarbonate, sodium thiosulfate, water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customto give a light green oil
  8. distillationDistillation in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-2e268c1b31fb4351950561eda9728d02
Source dataset
uspto-grants-1988_03
Patent number
US04729994

Reaction notes

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