Reaktion #460639

Reaktionsgleichung

(4-carbomethoxy) benzyltriphenylphosphonium bromide

methyl 4-formylbenzoate

sodium methoxide

toluene

→

compound

Ausbeute 72.0%

4,4'-bis(carbomethoxy)stilbene

Ausbeute 72.0%

Lösungsmittel

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 1 L 3-neck round bottom flask fitted with a glass stopper, rubber septum
2. 2
   Temperaturreflux condenser
3. 3
   Sonstigefitted with a nitrogen inlet tube
4. 4
   workup.DISSOLUTIONAfter the starting material dissolved
5. 5
   TemperaturThe reaction vessel was heated
6. 6
   Temperaturat reflux for 30 minutes
7. 7
   Temperaturthe reaction vessel was cooled at 0° C. for several hours
8. 8
   FiltrationThe resulting precipitate was filtered
9. 9
   Waschenwashed with 2:1 methanol
10. 10
    Trocknentoluene, and dried in a vacuum oven

Vorschrift

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.

Quelle