Acetone → 4-(4-Methoxyphenyl)but-3-en-2-one

HRID 714188

Reaktionsgleichung

Reaktionsgleichung von HRID 714188
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:11][C:12]([CH3:14])=[O:13].[OH-].[Na+].O>C(O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:11][C:12](=[O:13])[CH3:14])=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

Produkt 1

HCID 954144-(4-Methoxyphenyl)but-3-en-2-oneAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Methoxybenzaldehyde (1e, 0.63 ml, 5.2 mmol) and acetone (19, 4.00 ml, 54.0 mmol) were combined in ethanol (4 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (0.40 g, 10.0 mmol) and water (4 ml) was added dropwise and the mixture stirred for 1 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ether/hexane to give 0.57 g (62%) of a yellow solid: mp 71-73° C. [expected mp 68° C.]; 1H NMR: δ 2.34 (s, 3H), 3.83 (s, 3H), 6.59 (d, 1H, 0.1=16.3 Hz), 6.90 (d, 2H, J=8.7 Hz), 7.46 (d, 1H, J=16.3 Hz), 7.48 (d, 2H, J=8.7 Hz); 13C NMR: δ 27.5, 55.4, 114.4, 125.0, 127.1, 129.9, 143.1, 161.5, 198.1.

Aufarbeitung

  1. stirringthe mixture stirred for 1 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was recrystallized from ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e6478123efe24862922cb7c8b01d81d6
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187397B2

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