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

HRID 1732503Notes

Reaction equation

HRID 1732503 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-1octen 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. additionA mixture of 54.5 g
  2. temperaturerefluxed for 24 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is partitioned between water and ether
  7. washThe organic phase is washed with dilute sodium bicarbonate solution, brine
  8. dry with materialdried (MgSO4)
  9. customevaporated to an oil
  10. customThis material is used directly without purification

Sources & evidence

ORD record
ord-1e8883ae58484b208d5c41ca3855d58e
Source dataset
uspto-grants-1980_12
Patent number
US04237316

Reaction notes

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