Reaktion #47183

Reaktionsgleichung

Montmorillonite K10

cinnamaldehyde

DDQ

3-phenylpropanol

→

3-Phenylpropyl cinnamate

Ausbeute 84.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis taken in a round bottom flask
2. 2
   SonstigeAfter completion of the reaction (observed by TLC and by GC analysis)
3. 3
   Filtrationthe reaction mixture is filtered
4. 4
   Waschenwashed with ethylacetate (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 (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.

Quelle