반응 #47185

반응 방정식

2,4,5-trimethoxycinnamaldehyde

DDQ

MeOH

→

Methyl 2,4,5-trimethoxycinnamate

수율 84.0%

용매

toluene

반응 조건

후처리

1. 1
   기타is taken in a round bottom flask
2. 2
   온도The mixture is refluxed for 6 hrs under Dean Stark apparatus
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 MeOH (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 2,4,5-trimethoxycinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), MeOH (15 mL) and toluene (10 mL) is taken in a round bottom flask and catalytic amount of AMBERLITE® IR 120 (0.1 g) is added to it. The mixture is refluxed for 6 hrs under Dean Stark apparatus. After completion of the reaction (observed by TLC and by 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 2,4,5-trimethoxycinnamate (from formula I where X1═OCH3, X2═H, X3═OCH3, X4═OCH3, X5═H, R═CH3) is isolated in 84% yield. 1H-NMR (CDCl3, 300 MHz) δ7.91 (1H, d, J=16.10 Hz), 7.01 (1H, s), 6.50 (1H, s), 6.37 (1H, d, J=16.10 Hz), 3.93 (3H, s), 3.88 (3H, s), 3.87 (3H, s), 3.80 (3H, s); 13C-NMR (CDCl3, 75.4 MHz) δ168.2, 153.9, 151.9, 143.4, 139.7, 116.6, 115.4, 112.6, 96.9, 56.5, 56.4, 56.1, 51.5.

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