Reaction #47190

Reaction equation

15

Montmorillonite K10

cinnamaldehyde

DDQ

octanol

→

Octyl cinnamate

Yield 86.0%

Solvents

dioxane

Conditions

Workup

1. 1
   Otheris taken in a round bottom flask
2. 2
   TemperatureThe mixture is refluxed for 6 hrs under Dean Stark apparatus
3. 3
   OtherAfter completion of the reaction (observed by TLC and by GC analysis)
4. 4
   Filtrationthe reaction mixture is filtered
5. 5
   Washwashed with ethylacetate (5 ml×2)
6. 6
   ConcentrationConcentrate the filtrate under reduced pressure
7. 7
   Otherthe crude product thus obtained
8. 8
   Washeluted with diethyl ether

Procedure

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), octanol (15 mL) and dioxane (10 mL) is taken in a round bottom flask and catalytic amount of AMBERLYST® 15 (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 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. Octyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C8H17) is isolated in 86% yield. 1H-NMR (CDCl3, 300 MHz) δ7.51 (1H, d), 7.46 (2H, m), 7.26 (3H, m), 6.24 (1H, d), 3.93 (2H, m), 1.43 (2H, m), 1.16 (8H, m), 0.73 (5H, m); 13C-NMR (CDCl3, 75.4 MHz) δ166.5, 144.2, 134.4, 129.9, 128.6, 127.9, 118.2, 66.5, 38.8, 30.4, 28.9, 23.8, 22.9, 13.9, 10.9.

Source