Реакция #47182

Уравнение реакции

cinnamaldehyde

isopropanol

→

Isopropyl cinnamate

Выход 49.0%

Условия реакции

Обработка

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

Методика

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), Chloronil (22.5 mmol), isopropanol (10 mL) is taken in a round bottom flask and catalytic amount of silica gel (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. Isopropyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C3H8) is isolated in 49% yield. 1H-NMR (CDCl3, 300 MHz) δ7.59 (1H, d, J=16.55 Hz), 7.41 (2H, m), 7.27 (3H, m), 6.34 (1H, d, J=16.55 Hz), 5.07 (1H, m), 1.18 (6H, d); 13C-NMR (CDCl3, 75.4 MHz) δ166.4, 144.3, 134.5, 130.1, 128.6, 128.0, 118.8, 67.7, 21.9.

Источник