Sodium Iodide → 1-Iodooct-1-en-3-one
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
Product 1
Reagents, catalysts & solvents 1
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
- filtrationThe cooled mixture is filtered
- dissolutionThe residual oil is dissolved in benzene
- washthe solution is washed with 5% sodium thiosulfate solution, saturated sodium chloride solution
- customdried
- customThe residual oil is crystallized from hexane
Sources & evidence
- ORD record
- ord-bb1498b96cab4cd29c5b14219fc0b575
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04235797
Reaction notes
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