Reacción #47180

Ecuación de reacción

cinnamaldehyde

DDQ

→

Methyl cinnamate

Rendimiento 98.0%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrois taken in a round bottom flask
2. 2
   OtroAfter completion of the reaction (observed by TLC and GC analysis)
3. 3
   Filtraciónthe reaction mixture is filtered
4. 4
   Lavadowashed with MeOH (5 ml×2)
5. 5
   ConcentraciónConcentrate the filtrate under reduced pressure
6. 6
   Otrothe crude product thus obtained
7. 7
   Lavadoeluted with diethyl ether

Procedimiento

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.

Fuente