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

HRID 1248067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1248067
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[OH-].[Na+].[CH3:15][C:16]([CH3:18])=[O:17].Cl>CCCCCCC.C(O)(C)C.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:15][C:16](=[O:17])[CH:18]=[CH:7][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:11])[F:12])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Komponenten

8

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 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 8900HeptaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 4-trifluoromethylbenzaldehyde (64.2 g; 0.369 mol) in heptane (70 ml) is stirred under a nitrogen atmosphere, then sodium hydroxide (15 g; 10% aq), water (30 g), and bis(2-hydroxyethyl)tallowamine N-oxide (6 g) are added. Next a solution of acetone (10.7 g; 0.184 mol) in heptane (30 ml) is added at 25° C. to 35° C. over a period of two hours. The resulting slurry 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 and the mixture heated at reflux for 1.5 hours, and is then cooled to 20° C. The solid is filtered, washed with heptane (40 ml) and water, and is dried to afford 54.5 g of 99.9% pure title product (yield: 79.1%), mp 153° C. to 155° C.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationThe solid is filtered
  4. washwashed with heptane (40 ml) and water
  5. customis dried

Quellen und Nachweise

ORD-Eintrag
ord-f74230ace34a4f6188b8c24d0a9de6e2
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04521629

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