Reacción #47183

Ecuación de reacción

Montmorillonite K10

cinnamaldehyde

DDQ

3-phenylpropanol

→

3-Phenylpropyl cinnamate

Rendimiento 84.0%

Disolventes

toluene

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 by GC analysis)
3. 3
   Filtraciónthe reaction mixture is filtered
4. 4
   Lavadowashed with ethylacetate (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 (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.

Fuente