Acetone → 1,5-Bis(4-trifluoromethylphenyl)-penta-1,4-diene-3-one

HRID 1248068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1248068
[OH-].[Na+].[F:3][C:4]([F:14])([F:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[CH3:15][C:16]([CH3:18])=[O:17].Cl>CCCCCCC.C(O)(C)C>[F:3][C:4]([F:14])([F:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:15][C:16](=[O:17])[CH:18]=[CH:9][C:8]2[CH:7]=[CH:6][C:5]([C:4]([F:3])([F:13])[F:14])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 679964-(Trifluoromethyl)benzaldehyde

Produkt 1

HCID 5922411,5-Bis(4-trifluoromethylphenyl)-penta-1,4-diene-3-oneAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 8900HeptaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of sodium hydroxide (15 g of 10% aqueous) is added with stirring, and under a nitrogen atmosphere to a solution of 4-trifluoromethylbenzaldehyde (6.42 g; 0.369 mol) in heptane (70 ml). Next, a solution of acetone (10.7 g; 0.184 mol) in heptane (30 ml) is added to the above two phase system at a temperature range of from 25° C. to 30° C. over a period of two hours. The reaction mixture is then stirred for two hours at 25° C. to 30° C. Concentrated hydrochloric acid (9.4 ml) and isopropyl alcohol (48 ml) are then added, the mixture heated at reflux for 1.5 hours, and is then cooled to 20° C. The precipitated solid is filtered, washed with heptane (40 ml), and water and dried under vacuum to afford 50.8 g of title product, 98.8% pure, mp 154° C. to 156° C. (yield: 73.7%).

Aufarbeitung

  1. stirringThe reaction mixture is then stirred for two hours at 25° C. to 30° C
  2. temperaturethe mixture heated
  3. temperatureat reflux for 1.5 hours
  4. filtrationThe precipitated solid is filtered
  5. washwashed with heptane (40 ml), and water
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2312fb2aa5914a529f67b9146ca10b3b
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04521629

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