Sodium Iodide → 1-Iodooct-1-en-3-one

HRID 426606Notes

Reaction equation

HRID 426606 reaction equation
Cl[CH:2]=[CH:3][C:4](=[O:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[I-:11].[Na+]>CC(C)=O>[I:11][CH:2]=[CH:3][C:4](=[O:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 545149151-Chloro-1-octen-3-one

Product 1

HCID 534008741-Iodooct-1-en-3-oneYield 64.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 25 g (0.16 moles) of 1-chloro-1-octen-3-one (Example 187) and 35 g (0.23 moles) of sodium iodide in 200 ml of reagent acetone is stirred at the reflux temperature for 18 hours. The cooled mixture is filtered and the mother liquor taken to dryness. The residual oil is dissolved in benzene and the solution is washed with 5% sodium thiosulfate solution, saturated sodium chloride solution, dried and taken to dryness. The residual oil is crystallized from hexane to give 26 g of a white solid, mp 35°-37° C.; λ max 1670, 950 cm-1.

Workup

  1. filtrationThe cooled mixture is filtered
  2. dissolutionThe residual oil is dissolved in benzene
  3. washthe solution is washed with 5% sodium thiosulfate solution, saturated sodium chloride solution
  4. customdried
  5. customThe residual oil is crystallized from hexane

Sources & evidence

ORD record
ord-70623d9dbe64461b824d002513fbb940
Source dataset
uspto-grants-1979_10
Patent number
US04170597

Reaction notes

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