Hydrochloric Acid → 4'-Methoxyacetophenone

HRID 1603173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603173
COC1C=C(OC)C=CC=1C=[CH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22]C=C)=[CH:17][CH:16]=1)=[O:14].CC(C1C=CC(OCC=C)=CC=1)=O.COC1C=C(OC)C=CC=1C=O.Cl>C(O)C>[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:14]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 691752,4-DimethoxybenzaldehydeHCID 959691-(4-(2-Propen-1-yloxy)phenyl)ethanoneHCID 545548812,4-Dimethoxy-4'-(2-propenyloxy)chalcone

Produkt 1

HCID 74764'-MethoxyacetophenoneAusbeute 122,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Preparation of 2,4dimethoxy4'-prop-2-enyloxychalcone ##STR30## 0.88 g of 4-allyloxyacetophenone and 0.42 g of 2,4-dimethoxybenzaldehyde were dissolved in 3.5 ml of ethanol, and to the solution was added ethanol saturated with 3.5 ml of hydrogen chloride. The mixture was left at room temperature for 30 min during which time it turned heavily red. The solution was concentrated in vacuo and the residue chromatographed (column chromatography over silica gel 60 (Merck 0.0630-0.200 mm, 100 g), eluent toluene and toluene to which increasing amounts of ethyl acetate were added) to give 500 mg of 4-methoxyacetophenone and 471 mg of 2,4-dimethoxy-4'-prop-2-enyloxychone. The chalcone was recrystallized from petroleum ether-ethyl acetate to give 370 mg of slightly yellow crystals. For data, see Example 2.24.

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue chromatographed
  3. temperature(column chromatography over silica gel 60 (Merck 0.0630-0.200 mm, 100 g), eluent toluene and toluene to which increasing amounts of ethyl acetate were added)

Quellen und Nachweise

ORD-Eintrag
ord-19b2f443f3e9415c9e512c01c3c4f70e
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05985935

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