3-Phenylprop-2-Enal → 2-Hydroxyethyl cinnamate

HRID 18915Notes

Reaction equation

HRID 18915 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([C:13]1[C:19](=[O:20])C(Cl)=C(Cl)C(=O)C=1C#N)#N.O.[O-2].[O-2].[O-2].[O:29]=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>C(O)CO>[C:1]([O:29][CH2:13][CH2:19][OH:20])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 71586775Bentonite

Product 1

HCID 3503092-Hydroxyethyl cinnamateYield 88%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), ethylene glycol (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. 2-Hydroxyethyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C2H5O) is isolated in 88% yield. 1H-NMR (CDCl3, 300 MHz) δ7.65 (1H, d, J=16.55 Hz), 7.42 (2H, m), 7.29 (3H, m), 6.38 (1H, d, J=16.55 Hz), 4.37 (2H, t), 3.66 (2H, t); 13C-NMR (CDCl3, 75.4 MHz) δ166.4, 145.6, 134.2, 130.5, 128.9, 128.2, 117.3, 64.1, 41.8.

Workup

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

Sources & evidence

ORD record
ord-7153c88da5ed49fda3985f95cd9b739e
Source dataset
uspto-grants-2010_06
Patent number
US07741508B2

Reaction notes

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