3-Phenylprop-2-Enal → 2-Methoxyethyl cinnamate

HRID 18914

反応式

HRID 18914 の反応式
[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.[CH3:25][O:26][CH2:27][CH2:28][OH:29]>C1(C)C=CC=CC=1>[C:1]([O:29][CH2:28][CH2:27][O:26][CH3:25])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 3073-Phenylprop-2-EnalHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 80192-Methoxyethanol

生成物 1

HCID 687420242-Methoxyethyl cinnamate収率 93%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), 2-methoxyethanol (25 mL) and toluene (10 mL) is taken in a round bottom flask and catalytic amount of basic 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. 2-Methoxyethyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C3H7O) is isolated in 93% yield. 1H-NMR (CDCl3, 300 MHz) δ7.51 (1H, d, J=16.55 Hz), 7.28 (2H, m), 7.15 (3H, m), 6.28 (1H, d, J=16.55 Hz), 4.16 (2H, t), 3.44 (2H, t), 3.18 (3H, s); 13C-NMR (CDCl3, 75.4 MHz) δ166.6, 144.8, 134.3, 130.2, 128.8, 117.8, 70.4, 63.4, 58.7.

後処理

  1. customis taken in a round bottom flask
  2. additioncatalytic amount of basic 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

出典と根拠

ORDレコード
ord-0117e538717f41a2ba33491c7d96033e
出典データセット
uspto-grants-2010_06
特許番号
US07741508B2

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