Sodium Iodide → 4-(3-Iodopropoxy)benzoic acid, methyl ester

HRID 1450425Notes

Reaction equation

HRID 1450425 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.[I-:16].[Na+]>CC(C)=O.C(OCC)C>[I:16][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 12389265Methyl 4-(3-chloropropoxy)benzoate

Product 1

HCID 153374624-(3-Iodopropoxy)benzoic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

Dissolve 4-(3-chloropropoxy)benzoic acid, methyl ester (6.97 g, 30.5 mmol) in anhydrous acetone (100 mL) and add powdered sodium iodide (16.0 g, 107 mmol). Heat at reflux under an argon atmosphere for 38 hours. Dilute with ethyl ether (100 mL) and filter through Celite® filter aid. Wash the filtrate with water and brine, then dry (MgSO4). Evaporate the solvent in vacuo to give 4-(3iodopropoxy)benzoic acid, methyl ester as a yellow oil.

Workup

  1. temperatureHeat
  2. temperatureat reflux under an argon atmosphere for 38 hours
  3. filtrationfilter through Celite®
  4. filtrationfilter aid
  5. washWash the filtrate with water and brine
  6. dry with materialdry (MgSO4)
  7. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-892327d762e84237b0de3bfdce4143dc
Source dataset
uspto-grants-1997_02
Patent number
US05602147

Reaction notes

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