3-Phenylprop-2-Enal → Dodecyl 3-phenylprop-2-enoate

HRID 18913

Reaction equation

HRID 18913 reaction equation
[CH:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([OH:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[CH2:11]([O:23][C:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 3073-Phenylprop-2-EnalHCID 81931-Dodecanol

Product 1

HCID 53783116Dodecyl 3-phenylprop-2-enoateYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), SeO2 (11.3 mmol), dodecanol (5 mL) and toluene (10 mL) is taken in a round bottom flask and catalytic amount of neutral alumina (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. Dodecylcinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C12H25) is isolated in 87% yield. 1H-NMR (CDCl3, 300 MHz) δ7.51 (1H, d), 7.28 (2H, m), 7.14 (3H, m), 6.26 (1H, d), 4.02 (2H, t), 1.50 (2H, t), 1.11 (18H, m), 0.73 (3H, d); 13C-NMR (CDCl3, 75.4 MHz) δ166.4, 144.2, 134.4, 129.6, 128.6, 127.9, 118.2, 64.3, 31.9, 29.7, 29.6, 29.4, 28.7, 26.0, 22.7, 14.0.

Workup

  1. customis taken in a round bottom flask
  2. additioncatalytic amount of neutral alumina (0.1 g) is added to it
  3. temperatureThe mixture is refluxed for 6 hrs under Dean Stark apparatus
  4. customAfter completion of the reaction (observed by TLC and by GC analysis)
  5. filtrationthe reaction mixture is filtered
  6. washwashed with ethylacetate (5 ml×2)
  7. concentrationConcentrate the filtrate under reduced pressure
  8. customthe crude product thus obtained
  9. washeluted with diethyl ether

Sources & evidence

ORD record
ord-a1077639b9fd46aa98e7ceafa0337eb5
Source dataset
uspto-grants-2010_06
Patent number
US07741508B2

Linked notes

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