반응 #47180

반응 방정식

cinnamaldehyde

DDQ

→

Methyl cinnamate

수율 98.0%

용매

MeOH

반응 조건

후처리

1. 1
   기타is taken in a round bottom flask
2. 2
   기타After completion of the reaction (observed by TLC and GC analysis)
3. 3
   여과the reaction mixture is filtered
4. 4
   세척washed with MeOH (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 (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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