Sodium Iodide → 3-Methoxyphenethyl iodide
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe reaction mixture was refluxed for 2.5 hr
- customThe acetone was evaporated in vacuo
- dissolutionthe residue dissolved in ether
- washThe ether was washed with water, sodium bicarbonate, sodium thiosulfate, water and brine
- dry with materialdried over MgSO4
- customevaporated in vacuo
- customto give a light green oil
- 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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