Dimethylformamide → 4,4'-Bis(carbomethoxy)stilbene

HRID 2259454

Reaktionsgleichung

Reaktionsgleichung von HRID 2259454
CN([CH:4]=[O:5])C.[CH:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)=O.[CH3:18][O-:19].[Na+]>O>[C:8]1([CH:6]=[CH:6][C:8]2[CH:17]=[CH:16][C:11]([C:18]([O:5][CH3:4])=[O:19])=[CH:10][CH:9]=2)[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 15294Methyl 4-FormylbenzoateHCID 10942334Sodium Methoxide

Produkt 1

HCID 1391384,4'-Bis(carbomethoxy)stilbeneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

DMF (100 mL) and methyl 4-formylbenzoate (13.9 g, 0.13 mole) are added to the product solution from step (3) at a temperature of 25° to 28° C. Sodium methoxide (7 g) is added to the solution while maintaining the temperature at 25° to 35° C. by means of a water bath. The reaction mixture is heated at 25° to 35° C. for an additional 4 hours and then water (100 mL) is slowly added at 25° to 35° C. (with water bath cooling as necessary) to precipitate the product. After stirring for 1 hour, the product, dimethyl 4,4'-stilbenedicarboxylate, is collected by filtration, washed with water until the filtrate has a pH of 5 to 7 and then washed with methanol (2×50 mL). After drying at 60° C. under vacuum, dimethyl 4,4'-stilbenedicarboxylate is obtained in a 65% yield based on the amount of methyl 4-(hydroxymethyl)benzoate employed.

Aufarbeitung

  1. temperaturewhile maintaining the temperature at 25° to 35° C. by means of a water bath
  2. temperatureThe reaction mixture is heated at 25° to 35° C. for an additional 4 hours
  3. customto precipitate the product
  4. filtrationthe product, dimethyl 4,4'-stilbenedicarboxylate, is collected by filtration
  5. washwashed with water until the filtrate
  6. washwashed with methanol (2×50 mL)
  7. customAfter drying at 60° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d45c25bbef524c6993567be8ba3f7dfb
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05473098

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