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

HRID 2260124Notes

Reaction equation

HRID 2260124 reaction equation
C(OC)(=O)C1C=CC=CC=1.Cl[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.[I-:26].[Na+]>CC(C)=O.C(OCC)C>[I:26][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 7150Methyl BenzoateHCID 12389265Methyl 4-(3-chloropropoxy)benzoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

4-[3-4-[(2-Benzothiazolyl )carbonyl]-1-piperidinyl]propoxy]benzoic acid, methyl ester ##STR22## 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-(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-921952242f0b405b8177b3d6665f7244
Source dataset
uspto-grants-1995_12
Patent number
US05476861

Reaction notes

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