Reaktion #47180

Reaktionsgleichung

cinnamaldehyde

DDQ

→

Methyl cinnamate

Ausbeute 98.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis taken in a round bottom flask
2. 2
   SonstigeAfter completion of the reaction (observed by TLC and GC analysis)
3. 3
   Filtrationthe reaction mixture is filtered
4. 4
   Waschenwashed with MeOH (5 ml×2)
5. 5
   EinengenConcentrate the filtrate under reduced pressure
6. 6
   Sonstigethe crude product thus obtained
7. 7
   Wascheneluted with diethyl ether

Vorschrift

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.

Quelle