Реакция #47187

Уравнение реакции

cinnamaldehyde

DDQ

MeOH

→

Methyl cinnamate

Выход 96.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   Другоеis taken in a round bottom flask
2. 2
   workup.ADDITIONcatalytic amount of neutral alumina (0.1 g) is added to it
3. 3
   ТемператураThe mixture is refluxed for 6 hrs under Dean Stark apparatus
4. 4
   ДругоеAfter completion of the reaction (observed by TLC and by GC analysis)
5. 5
   Фильтрацияthe reaction mixture is filtered
6. 6
   Промывкаwashed with MeOH (5 ml×2)
7. 7
   КонцентрированиеConcentrate the filtrate under reduced pressure
8. 8
   Другоеthe crude product thus obtained
9. 9
   Промывкаeluted with diethyl ether

Методика

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.

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