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

HRID 18909

반응식

HRID 18909 반응식
[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>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

참가 물질

5

반응물 3

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

생성물 1

HCID 76442-Propenoic acid, 3-phenyl-, methyl ester수율 96%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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 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 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 96% yield whose NMR values are found matching with reported values as in example 1.

후처리

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

출처 및 근거

ORD 기록
ord-2ff568415842448c822db86cfe692f73
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741508B2

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