反応 #47183

反応方程式

Montmorillonite K10

cinnamaldehyde

DDQ

3-phenylpropanol

→

3-Phenylpropyl cinnamate

収率 84.0%

溶媒

toluene

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 by GC analysis)
3. 3
   ろ過the reaction mixture is filtered
4. 4
   洗浄washed with ethylacetate (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 (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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