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

HRID 373457

Reaktionsgleichung

Reaktionsgleichung von HRID 373457
[Br-].[C:2]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)([O:4][CH3:5])=[O:3].[CH:32]([C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)=O.C1(C)C=CC=CC=1.C[O-].[Na+]>CO>[C:38]([C:37]1[CH:42]=[CH:43][C:34]([CH:32]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]([C:2]([O:4][CH3:5])=[O:3])=[CH:31][CH:30]=2)=[CH:35][CH:36]=1)([O:40][CH3:41])=[O:39]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 15294Methyl 4-FormylbenzoateHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 10942334Sodium Methoxide

Produkt 1

HCID 1391384,4'-Bis(carbomethoxy)stilbeneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a 1 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser fitted with a nitrogen inlet tube, was added 20.0 g (39.77 mmol) (4-carbomethoxy) benzyltriphenylphosphonium bromide; 7.83 g (47.73 mmol) methyl 4-formylbenzoate; and 110 mL 2:1 methanol: toluene. After the starting material dissolved, 10.0 mL (43.75 mmol) 25% sodium methoxide solution in methanol was added dropwise over several minutes. The reaction vessel was heated at reflux for 30 minutes. After cooling to room temperature, the reaction vessel was cooled at 0° C. for several hours. The resulting precipitate was filtered, washed with 2:1 methanol: toluene, and dried in a vacuum oven to afford 5.54 g (72%) of the compound as a 57:43 mixture of cis: trans isomers.

Aufarbeitung

  1. customTo a 1 L 3-neck round bottom flask fitted with a glass stopper, rubber septum
  2. temperaturereflux condenser
  3. customfitted with a nitrogen inlet tube
  4. dissolutionAfter the starting material dissolved
  5. temperatureThe reaction vessel was heated
  6. temperatureat reflux for 30 minutes
  7. temperaturethe reaction vessel was cooled at 0° C. for several hours
  8. filtrationThe resulting precipitate was filtered
  9. washwashed with 2:1 methanol
  10. dry with materialtoluene, and dried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-cdafc08746c54bb2b0d1586fd2da73e7
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164100

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