Reaction equation
[CH:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[C:25]1([CH2:31][CH2:32][CH2:33][OH:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>C1(C)C=CC=CC=1>[C:1]([O:34][CH2:33][CH2:32][CH2:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
Procedure
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.
Workup
- customis taken in a round bottom flask
- customAfter completion of the reaction (observed by TLC and by GC analysis)
- filtrationthe reaction mixture is filtered
- washwashed with ethylacetate (5 ml×2)
- concentrationConcentrate the filtrate under reduced pressure
- customthe crude product thus obtained
- washeluted with diethyl ether
Sources & evidence
- ORD record
- ord-5eb17a058034414b97ff394a3f231f25
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741508B2
Linked notes
Loading…