Sodium Iodide → Ethyl 4-(3-iodopropoxy)benzoate

HRID 2268482Notes

Reaction equation

HRID 2268482 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]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 18348522Ethyl 4-(3-chloropropoxy)benzoate

Product 1

HCID 18348598Ethyl 4-(3-iodopropoxy)benzoateYield 94.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

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

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hr
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with 5% aqueous sodium sulfite, water, saturated aqueous sodium chloride
  5. customdried
  6. 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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