Vanillin → HCID 52848434, Verbindung

HRID 2221572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221572
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH3:14].[O:15]=[CH:16][C:17]1[CH:25]=[CH:24][C:22]([OH:23])=[C:19]([O:20][CH3:21])[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:21][O:20][C:19]1[CH:18]=[C:17]([CH:25]=[CH:24][C:22]=1[O:23][CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH3:14])[CH:16]=[O:15]

Komponenten

6

Edukt 4

HCID 1183VanillinHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 123072505-(Chloromethyl)-4-methyl-2-phenyl-1,3-thiazole

Produkt 1

HCID 52848434HCID 52848434, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 5-chloromethyl-4-methyl-2-phenyl-1,3-thiazole (2.30 g), vanillin (1.49 g), potassium carbonate (1.35 g) and N,N-dimethylformamide (50 mL) was stirred at 90° C. for 3 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 3-methoxy-4-[(4-methyl-2-phenyl-1,3-thiazol-5-yl)methoxy]benzaldehyde as pale-yellow crystals (3.02 g, yield 91%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 118-119° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-be99b7ad6d584d999e92f8f19caae033
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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