Acetone → Dibenzylidene acetone

HRID 77650

Reaktionsgleichung

Reaktionsgleichung von HRID 77650
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:12])=[O:11].[OH-].[Na+].O>C(O)C>[C:2]1([CH:1]=[CH:9][C:10](=[O:11])[CH:12]=[CH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 240BenzaldehydeHCID 962WaterHCID 14798Sodium Hydroxide

Produkt 1

HCID 95417Dibenzylidene acetoneAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Benzaldehyde (1b, 2.54 ml, 25.0 mmol) and acetone (19, 0.90 ml, 12.2 mmol) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (2.50 g, 62.5 mmol) and water (25 ml) was added and the solution stirred for 3 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethanol to afford 2.35 g (82%) of yellow crystals: mp 110-112° C. [expected mp 112-114° C.]; 1H NMR: δ 7.07 (d, 2H, J=15.9 Hz), 7.40 (m, 8H), 7.61 (m, 2H), 7.73 (d, 2H, J=15.9 Hz); 13C NMR: δ 125.4, 128.3, 12.9, 130.4, 134.7, 143.2, 188.7.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a285b0cb32b14930afc6ec42c7e20e21
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841326B2

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