Sodium Iodide → Ethyl 2-(4-iodomethylphenyl)propionate

HRID 971877Notes

Reaction equation

HRID 971877 reaction equation
[I-:1].[Na+].Cl[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1>C(C(C)=O)C>[I:1][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 10998728Ethyl 2-[4-(chloromethyl)phenyl]propanoate

Product 1

HCID 21312279Ethyl 2-(4-iodomethylphenyl)propionateYield 92.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

After a solution of 15 g of sodium iodide in 140 ml of methyl ethyl ketone was refluxed for 1 hour, 12.5 g of ethyl 2-(4-chloromethylphenyl)propionate was added and refluxing was continued for further 8 hours. After the reaction was completed, methyl ethyl ketone was removed by distillation from the reaction mixture under reduced pressure, the residue was poured into ice-water and extracted with ether. The extract was washed with water and an aqueous sodium thiosulfate solution, successively, dried, and the solvent was evaporated to give 16.3 g of the desired compound as an oily and slightly yellow substance.

Workup

  1. temperaturerefluxing
  2. custommethyl ethyl ketone was removed by distillation from the reaction mixture under reduced pressure
  3. additionthe residue was poured into ice-water
  4. extractionextracted with ether
  5. washThe extract was washed with water
  6. dry with materialan aqueous sodium thiosulfate solution, successively, dried
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c0f1b88487d24e98af411591788751f4
Source dataset
uspto-grants-1979_07
Patent number
US04161538

Reaction notes

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