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

HRID 234701Notes

Reaction equation

HRID 234701 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 (6.97g, 30.5mmol) in anhydrous acetone (100mL) and add powdered sodium iodide (16.0g, 107mmol). Heat at reflux under an argon atmosphere for 38 hours. Dilute with ethyl ether (100mL) and filter through Celite® filter aid. Wash the filtrate with water and brine, then dry (MgSO4). Evaporate the solvent in vacuo to give 4-(3-iodopropoxy)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-07f6edb81f394a1ba942dda25a292812
Source dataset
uspto-grants-1997_01
Patent number
US05596003

Reaction notes

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