反応 #47180

反応方程式

cinnamaldehyde

DDQ

→

Methyl cinnamate

収率 98.0%

溶媒

MeOH

反応条件

後処理

1. 1
   その他is taken in a round bottom flask
2. 2
   その他After completion of the reaction (observed by TLC and GC analysis)
3. 3
   ろ過the reaction mixture is filtered
4. 4
   洗浄washed with MeOH (5 ml×2)
5. 5
   濃縮Concentrate the filtrate under reduced pressure
6. 6
   その他the crude product thus obtained
7. 7
   洗浄eluted with diethyl ether

実験手順

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.

出典