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

HRID 18905

반응식

HRID 18905 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(=O)C=1C#N)#N.[C:25]1([CH2:31][CH2:32][CH2:33][OH:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>C1(C)C=CC=CC=1>[C:1]([O:34][CH2:33][CH2:32][CH2:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 3073-Phenylprop-2-EnalHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 31234BenzenepropanolHCID 71586775Bentonite

생성물 1

HCID 610512-Propenoic acid, 3-phenyl-, 3-phenylpropyl ester수율 84%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (22.5 mmol), 3-phenylpropanol (10 mL) and toluene (10 mL) is taken in a round bottom flask and catalytic amount of Montmorillonite K10 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 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. 3-Phenylpropyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C9H11) is isolated in 84% yield. 1H-NMR (CDCl3, 300 MHz) δ7.74 (1H, d), 7.43 (2H, m), 7.28 (5H, m), 7.19 (3H, m), 6.48 (2H, d), 4.22 (2H, t), 2.69 (2H, t), 1.98 (2H, t); 13C-NMR (CDCl3, 75.4 MHz) δ166.7, 144.7, 141.4, 134.6, 130.6, 129.2, 128.6, 127.4, 126.5, 118.4, 63.9, 32.3, 30.5.

후처리

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

출처 및 근거

ORD 기록
ord-5eb17a058034414b97ff394a3f231f25
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741508B2

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