3-Phenylprop-2-Enal → 2-Propenoic acid, 3-phenyl-, methyl ester

HRID 18902

Reaction equation

HRID 18902 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:15](=[O:16])C=1C#N)#N>CO>[C:1]([O:16][CH3:15])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3073-Phenylprop-2-EnalHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Product 1

HCID 76442-Propenoic acid, 3-phenyl-, methyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), MeOH (15 mL) is taken in a round bottom flask and catalytic amount of AMBERLYST® 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 GC analysis), the reaction mixture is filtered and washed with MeOH (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. Methyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═CH3) is isolated in 98% yield. 1H-NMR (CDCl3, 300 MHz) δ7.56 (1H, d, J=16.55 Hz), 7.34 (2H, m), 7.21 (3H, m), 6.31 (1H, d, J=16.55 Hz), 3.64 (3H, s); 13C-NMR (CDCl3, 75.4 MHz) δ167.2, 144.7, 134.3, 130.2, 128.8, 128.0, 117.8, 51.5.

Workup

  1. customis taken in a round bottom flask
  2. customAfter completion of the reaction (observed by TLC and GC analysis)
  3. filtrationthe reaction mixture is filtered
  4. washwashed with MeOH (5 ml×2)
  5. concentrationConcentrate the filtrate under reduced pressure
  6. customthe crude product thus obtained
  7. washeluted with diethyl ether

Sources & evidence

ORD record
ord-c1abab38dd8a41428d390adb933816b9
Source dataset
uspto-grants-2010_06
Patent number
US07741508B2

Linked notes

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