Реакция #47183

Уравнение реакции

Montmorillonite K10

cinnamaldehyde

DDQ

3-phenylpropanol

→

3-Phenylpropyl cinnamate

Выход 84.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   Другоеis taken in a round bottom flask
2. 2
   ДругоеAfter completion of the reaction (observed by TLC and by GC analysis)
3. 3
   Фильтрацияthe reaction mixture is filtered
4. 4
   Промывкаwashed with ethylacetate (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 (22.5 mmol), 3-phenylpropanol (10 mL) and toluene (10 mL) is taken in a round bottom flask and catalytic amount of Montmorillonite K10 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 by GC analysis), the reaction mixture is filtered and washed with ethylacetate (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. 3-Phenylpropyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C9H11) is isolated in 84% yield. 1H-NMR (CDCl3, 300 MHz) δ7.74 (1H, d), 7.43 (2H, m), 7.28 (5H, m), 7.19 (3H, m), 6.48 (2H, d), 4.22 (2H, t), 2.69 (2H, t), 1.98 (2H, t); 13C-NMR (CDCl3, 75.4 MHz) δ166.7, 144.7, 141.4, 134.6, 130.6, 129.2, 128.6, 127.4, 126.5, 118.4, 63.9, 32.3, 30.5.

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