Diethyl Malonate → 5-(2-Fluoro-5-methylphenyl)cyclohexane-1,3-dione

HRID 1700717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1700717
[O-:1][CH2:2][CH3:3].[Na+].C(OCC)(=O)CC(OCC)=O.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH:24]=[CH:25][C:26](=[O:28])[CH3:27]>C(O)C>[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH:24]1[CH2:3][C:2](=[O:1])[CH2:27][C:26](=[O:28])[CH2:25]1

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 539200784-(2-Fluoro-5-methylphenyl)-3-buten-2-one

Produkt 1

HCID 183174315-(2-Fluoro-5-methylphenyl)cyclohexane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 20% sodium ethoxide in ethanol (1.4 g) was added at room temperature diethyl malonate (3.3 g) and then was added little by little 4-(2-fluoro-5-methylphenyl)-3-buten-2-one (3.5 g), and the reaction mixture was stirred at room temperature for 30 minutes, refluxed for 2 hours and cooled. The solvent was evaporated, and to the residue was added water. The aqueous layer was washed with ethyl acetate and concentrated. To the residue was added 2M sodium hydroxide (11 ml), and the mixture was refluxed for 2 hours and cooled. To the mixture was added 2.5M sulfuric acid (11 ml) for 5 minutes, and the mixture was refluxed for 30 minutes and cooled. Precipitated crystals were filtered, washed with water and isopropylether to give 5-(2-fluoro-5-methylphenyl)cyclohexane-1,3-dione (1.6 g) as colorless crystals.

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. temperaturecooled
  3. customThe solvent was evaporated
  4. additionto the residue was added water
  5. washThe aqueous layer was washed with ethyl acetate
  6. concentrationconcentrated
  7. additionTo the residue was added 2M sodium hydroxide (11 ml)
  8. temperaturethe mixture was refluxed for 2 hours
  9. temperaturecooled
  10. additionTo the mixture was added 2.5M sulfuric acid (11 ml) for 5 minutes
  11. temperaturethe mixture was refluxed for 30 minutes
  12. temperaturecooled
  13. customPrecipitated crystals
  14. filtrationwere filtered
  15. washwashed with water and isopropylether

Quellen und Nachweise

ORD-Eintrag
ord-389d8f72a2284b97b990a5c0af487823
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350749B1

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