Sodium Iodide → (E)-1-Iodo-1-octen-3-one

HRID 649076Notes

Reaction equation

HRID 649076 reaction equation
[I-:1].[Na+].Cl/[CH:4]=[CH:5]/[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>CC(C)=O>[I:1]/[CH:4]=[CH:5]/[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 110410031-Chloro-trans-1-octen-3-one

Product 1

HCID 11139597(E)-1-Iodo-1-octen-3-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 54.5 g (0.364 mole) of sodium iodide and 40 g. (0.249 mole) of 1-chloro-trans-1-octen 3-one (Example 18) in 360 ml. of acetone is stirred and refluxed for 24 hours. The reaction mixture is cooled, filtered and concentrated. The residue is partitioned between water and ether. The organic phase is washed with dilute sodium bicarbonate solution, brine, dried (MgSO4) and evaporated to an oil. This material is used directly without purification.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is partitioned between water and ether
  6. washThe organic phase is washed with dilute sodium bicarbonate solution, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to an oil
  9. customThis material is used directly without purification

Sources & evidence

ORD record
ord-eaaed4f8bdc741bd9e1d9f93a1e8a4f8
Source dataset
uspto-grants-1988_04
Patent number
US04737590

Reaction notes

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