Sodium Iodide → Ethyl 4-(3-iodopropoxy)benzoate
Reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1.[I-:17].[Na+]>CC(C)=O.O>[I:17][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
The mixture of ethyl 4-(3-chloropropoxy)benzoate (26.5 g), sodium iodide (49.0 g) in acetone (300 ml) was heated under reflux for 24 hr. The reaction mixture was diluted with water and extracted with diethyl ether. The organic layer was washed with 5% aqueous sodium sulfite, water, saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo to yield the entitled compound (34.4 g) as an oil.
Workup
- temperaturewas heated
- temperatureunder reflux for 24 hr
- extractionextracted with diethyl ether
- washThe organic layer was washed with 5% aqueous sodium sulfite, water, saturated aqueous sodium chloride
- customdried
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-958417d83ed94a4db4d810fec83bf7a6
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326369B1
Reaction notes
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