Water → HCID 20063420, compound

HRID 1084346Notes

Reaction equation

HRID 1084346 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

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

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 25 hours
  3. customthe toluene layer was separated
  4. extractionThe aqueous layer was extracted twice with ether
  5. washThis mixture was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. 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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