Реакция #47180

Уравнение реакции

cinnamaldehyde

DDQ

→

Methyl cinnamate

Выход 98.0%

Растворители

MeOH

Условия реакции

Обработка

1. 1
   Другоеis taken in a round bottom flask
2. 2
   ДругоеAfter completion of the reaction (observed by TLC and GC analysis)
3. 3
   Фильтрацияthe reaction mixture is filtered
4. 4
   Промывкаwashed with MeOH (5 ml×2)
5. 5
   КонцентрированиеConcentrate the filtrate under reduced pressure
6. 6
   Другоеthe crude product thus obtained
7. 7
   Промывкаeluted with diethyl ether

Методика

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), MeOH (15 mL) is taken in a round bottom flask and catalytic amount of AMBERLYST® 15 (0.1 g) is added to it. The mixture is stirred for 20 hrs at room temperature. After completion of the reaction (observed by TLC and 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 (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═CH3) is isolated in 98% yield. 1H-NMR (CDCl3, 300 MHz) δ7.56 (1H, d, J=16.55 Hz), 7.34 (2H, m), 7.21 (3H, m), 6.31 (1H, d, J=16.55 Hz), 3.64 (3H, s); 13C-NMR (CDCl3, 75.4 MHz) δ167.2, 144.7, 134.3, 130.2, 128.8, 128.0, 117.8, 51.5.

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