반응 #47183

반응 방정식

Montmorillonite K10

cinnamaldehyde

DDQ

3-phenylpropanol

→

3-Phenylpropyl cinnamate

수율 84.0%

용매

toluene

반응 조건

후처리

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

실험 절차

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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