Acetone → 1,5-Bis(2-trifluoromethylphenyl)-1,4-pentadien-3-one

HRID 714173

Reaktionsgleichung

Reaktionsgleichung von HRID 714173
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:13][C:14]([CH3:16])=[O:15].[OH-].[Na+].O>C(O)C>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[CH:13][C:14](=[O:15])[CH:16]=[CH:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[C:2]([F:1])([F:11])[F:12]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 123067o-(Trifluoromethyl)benzaldehyde

Produkt 1

HCID 854340791,5-Bis(2-trifluoromethylphenyl)-1,4-pentadien-3-oneAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-(Trifluoromethyl)-benzaldehyde (1w, 0.75 ml, 5.7 mmol) and acetone (19, 0.21 ml, 2.8 mmol) were combined in ethanol (20 ml) and stirred for 10 min at room temperature. A solution of sodium hydroxide (0.34 g, 8.5 mmol) and water (15 ml) was added and the mixture stirred for 18 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethanol to afford 0.92 g (87%) of a yellow solid: mp 131-133° C. [expected mp 131° C.]; 1H NMR: δ 6.99 (d, 2H, J=15.9 Hz), 7.48 (t, 2H, J=7.6 Hz), 7.56 (t, 2H, J=7.0 Hz), 7.70 (d, 2H, J=7.7 Hz), 7.77 (d, 2H, J=7.6 Hz), 8.07 (d, 2H, J=15.7 Hz); 13C NMR: δ 123.9, 126.2, 127.9, 128.8, 129.4, 129.7, 132.1, 133.7, 139.1, 188.0.

Aufarbeitung

  1. stirringthe mixture stirred for 18 hr at room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4da9f86573cc4d1ba9c30cdb355a2b03
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187397B2

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