반응 #47182

반응 방정식

cinnamaldehyde

isopropanol

→

Isopropyl cinnamate

수율 49.0%

반응 조건

후처리

1. 1
   기타is taken in a round bottom flask
2. 2
   workup.ADDITIONcatalytic amount of silica gel (0.1 g) is added to it
3. 3
   기타After completion of the reaction (observed by TLC and by GC analysis)
4. 4
   여과the reaction mixture is filtered
5. 5
   세척washed with ethylacetate (5 ml×2)
6. 6
   농축Concentrate the filtrate under reduced pressure
7. 7
   기타the crude product thus obtained
8. 8
   세척eluted with diethyl ether

실험 절차

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.

출처