Reaktion #47187

Reaktionsgleichung

cinnamaldehyde

DDQ

MeOH

→

Methyl cinnamate

Ausbeute 96.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis taken in a round bottom flask
2. 2
   workup.ADDITIONcatalytic amount of neutral alumina (0.1 g) is added to it
3. 3
   TemperaturThe mixture is refluxed for 6 hrs under Dean Stark apparatus
4. 4
   SonstigeAfter completion of the reaction (observed by TLC and by GC analysis)
5. 5
   Filtrationthe reaction mixture is filtered
6. 6
   Waschenwashed with MeOH (5 ml×2)
7. 7
   EinengenConcentrate the filtrate under reduced pressure
8. 8
   Sonstigethe crude product thus obtained
9. 9
   Wascheneluted with diethyl ether

Vorschrift

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), MeOH (15 mL) and toluene (10 mL) is taken in a round bottom flask and catalytic amount of neutral alumina (0.1 g) is added to it. The mixture is refluxed for 6 hrs under Dean Stark apparatus. After completion of the reaction (observed by TLC and by GC analysis), the reaction mixture is filtered and washed with MeOH (5 ml×2). Concentrate the filtrate under reduced pressure and the crude product thus obtained is loaded on a neutral alumina column and eluted with diethyl ether. Methyl cinnamate is isolated in 96% yield whose NMR values are found matching with reported values as in example 1.

Quelle