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

HRID 18908

反応式

HRID 18908 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:15](=[O:16])C=1C#N)#N.CO>C(O)(=O)C.C1(C)C=CC=CC=1>[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

参加物

6

反応物 3

HCID 3073-Phenylprop-2-EnalHCID 887MethanolHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone

生成物 1

HCID 76442-Propenoic acid, 3-phenyl-, methyl ester収率 98%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 1140Toluene溶媒

実験手順

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), MeOH (15 mL) and toluene (10 mL) is taken in a round bottom flask and catalytic amount of acetic acid (5 drops) 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 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 is isolated in 98% yield whose NMR values are found matching with reported values as in example 1.

後処理

  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 MeOH (5 ml×2)
  6. concentrationConcentrate the filtrate under reduced pressure
  7. customthe crude product thus obtained
  8. washeluted with diethyl ether

出典と根拠

ORDレコード
ord-8c6ec4a7b7534daba73192fbd522e4cc
出典データセット
uspto-grants-2010_06
特許番号
US07741508B2

関連ノート

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