Water → HCID 20063420, compound
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]=[C:6]([F:9])[CH:7]=[O:8].[Na].C1(S)C=CC=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[C:6](\[F:9])/[CH:7]=[O:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2.35 Grams of 6-chloro-2-fluoro-2-hexenal (E form : Z form =6.8 : 1) was dissolved in 20 ml of dry toluene, and after adding 10 mg of the sodium salt of thiophenol, the resulting solution was heated under reflux for 25 hours with stirring. Thereafter, 10 ml of water was added to the reaction solution, and the toluene layer was separated. The aqueous layer was extracted twice with ether, and the ether extracts were combined with the above toluene layer. This mixture was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 2.35 g of (Z)-6-chloro-2-fluoro-2-hexenal.
Workup
- temperaturethe resulting solution was heated
- temperatureunder reflux for 25 hours
- customthe toluene layer was separated
- extractionThe aqueous layer was extracted twice with ether
- washThis mixture was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-591c4c22e5d049b8966011d5b8d6af29
- Source dataset
- uspto-grants-1991_04
- Patent number
- US05004753
Reaction notes
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