Acetone → 4-(2,3,4,5-Tetramethoxy-6-methylphenyl)but-3-en-2-one

HRID 2166243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2166243
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[C:8]([O:15][CH3:16])=[C:7]([CH3:17])[C:4]=1[CH:5]=O.[CH3:18][C:19]([CH3:21])=[O:20].C[O-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:4]([CH:5]=[CH:18][C:19](=[O:20])[CH3:21])=[C:7]([CH3:17])[C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 10942334Sodium MethoxideHCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehyde

Produkt 1

HCID 542361174-(2,3,4,5-Tetramethoxy-6-methylphenyl)but-3-en-2-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2,3,4,5-tetramethoxy-6-methylbenzaldehyde (1.56 g, 6.5 mmol) and acetone (1.13 g, 19.5 mmol) in methanol (15 ml) was added 28% methanolic sodium methoxide (1.88 g). The mixture was refluxed for 1.5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was chromatographed ona silica gel column elution being carried out with isopropyl ether. The fractions containing the desired compound were concentrated to give 1,2,3,4-tetramethoxy-5-methyl-6-(3-oxo-1-butenyl)benzene (Compound 21, 1.09 g, 60% Oily substance) δ 2.28 (3H), 2.36 (3H), 3.77 (3H), 3.79 (3H), 3.89 (3H), 3.95 (3H), 6.70 (1H), 7.57 (1H),

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. customAfter completion of the reaction
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was chromatographed ona
  5. washsilica gel column elution
  6. additionThe fractions containing the desired compound
  7. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-52ba1c8b681c4e479e09e394ffeb08eb
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04943645

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