3-Phenylprop-2-Enal → Octylcinnamate

HRID 18912

反応式

HRID 18912 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.[CH2:25]([OH:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>O1CCOCC1>[C:1]([O:33][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[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 4

HCID 3073-Phenylprop-2-EnalHCID 9571-OctanolHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 71586775Bentonite

生成物 1

HCID 3017905Octylcinnamate収率 86%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), octanol (15 mL) and dioxane (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. Octyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C8H17) is isolated in 86% yield. 1H-NMR (CDCl3, 300 MHz) δ7.51 (1H, d), 7.46 (2H, m), 7.26 (3H, m), 6.24 (1H, d), 3.93 (2H, m), 1.43 (2H, m), 1.16 (8H, m), 0.73 (5H, m); 13C-NMR (CDCl3, 75.4 MHz) δ166.5, 144.2, 134.4, 129.9, 128.6, 127.9, 118.2, 66.5, 38.8, 30.4, 28.9, 23.8, 22.9, 13.9, 10.9.

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 ethylacetate (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-a62278bbe0bf49dca693fa8400444f31
出典データセット
uspto-grants-2010_06
特許番号
US07741508B2

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