Sodium Iodide → HCID 21313737, compound

HRID 236862Notes

Reaction equation

HRID 236862 reaction equation
[CH:1]1([C:7](=[O:11])/[CH:8]=[CH:9]/Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[I-:12].[Na+]>CC(C)=O>[CH:1]1([C:7](=[O:11])/[CH:8]=[CH:9]/[I:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 12801553HCID 12801553, compound

Product 1

HCID 21313737HCID 21313737, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 153 g of (25C) and 500 g of sodium iodide in 700 ml of dry acetone (distilled from anhydrous potassium carbonate) was refluxed under argon for 18 hours. The solvent was then removed by evaporation in vacuo. The residue was mixed with water and extracted three times with ether. The combined extract was dried over anhydrous magnesium sulfate and then evaporated in vacuo to yield 238 g of the desired product which had the following spectral properties: nmr (CDCl3) δ 0.9-2.8 (11H, m), 7.30 (1H, d, J=15 Hz) and 7.92 ppm (1H, d, J=15 Hz).

Workup

  1. customThe solvent was then removed by evaporation in vacuo
  2. additionThe residue was mixed with water
  3. extractionextracted three times with ether
  4. extractionThe combined extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-56f932318cd5430eb9dde8fb94fad41a
Source dataset
uspto-grants-1979_06
Patent number
US04158018

Reaction notes

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