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

HRID 77669

Reaktionsgleichung

Reaktionsgleichung von HRID 77669
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14]([CH3:16])=[O:15].[OH-].[Na+].O>C(O)C>[C:1]1([CH:11]=[CH:13][C:14](=[O:15])[CH:16]=[CH:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 962WaterHCID 61951-NaphthaldehydeHCID 14798Sodium Hydroxide

Produkt 1

HCID 5925121,5-Bis(1-naphthyl)-1,4-pentadien-3-oneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1-Naphthaldehyde (22, 1.36 ml, 10.0 mmol) and acetone (19, 0.37 ml, 5.0 mmol) were combined in ethanol (10 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (0.40 g, 10.0 mmol) and water (10 ml) was added and the mixture stirred for 18 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethyl acetate to give 0.63 g (38%) of a yellow solid: mp 132-133° C. [expected mp 128° C.]; 1H NMR: δ 7.24 (d, 2H, J=15.7 Hz), 7.57 (m, 6H), 7.92 (m, 6H), 8.28 (d, 2H, J=8.0 Hz), 8.65 (d, 2H, J=15.5 Hz); 13C NMR: δ 123.4, 125.1, 125.4, 126.2, 126.9, 128.1, 128.7, 130.7, 131.7, 132.2, 133.7, 140.3, 188.5.

Aufarbeitung

  1. stirringthe mixture stirred for 18 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. filtrationfiltered
  5. customevaporated
  6. customto afford a solid
  7. customThe crude solid was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5793ccc1061342aabbd3ef45a1c777b5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841326B2

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