Sodium Iodide → HCID 57444584, compound

HRID 860498Notes

Reaction equation

HRID 860498 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12]Cl)(=[O:3])[CH3:2].[I-:14].[Na+]>CC(C)=O>[C:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][I:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium Iodide2×HCID 4053372HCID 4053372, compound

Product 1

HCID 57444584HCID 57444584, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-[2-(2-chloroethoxy)ethoxy]ethyl acetate (6.23 g) and sodium iodide (22.2 g) in acetone (60 mL) was refluxed for 4 hours. The mixture was further refluxed for 4 hours after adding sodium iodide (11.0 g). The solvent was evaporated off, and the residue was partitioend between EtOAc (50 mL) and water (50 mL). The aqueous layer was washed with 10% sodium thiosulfate and brine, dried over MgSO4, and evaporated to give 2-[2-(2-iodoethoxy)ethoxy]ethyl acetate as a pale yellow oil (9.74 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe mixture was further refluxed for 4 hours
  3. customThe solvent was evaporated off
  4. washThe aqueous layer was washed with 10% sodium thiosulfate and brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-221f4039030349c69614d0eb71b918bc
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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