Methanol → 4-Methoxycinnamate methyl ester

HRID 18906

反応式

HRID 18906 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][CH:9]=[O:10])=[CH:5][CH:4]=1.C(C1C(=O)C(Cl)=C(Cl)[C:17](=[O:18])C=1C#N)#N.CO>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][C:9]([O:18][CH3:17])=[O:10])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 887MethanolHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 2309953-(4-Methoxyphenyl)prop-2-enal

生成物 1

HCID 928414-Methoxycinnamate methyl ester収率 91%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A homogeneous mixture containing 4-methoxycinnamaldehyde (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 AMBERLITE® IR 400 (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 4-methoxycinnamate (from formula I where X1═H, X2═H, X3═OCH3, X4═H, X5═H, R═CH3) is isolated in 91% yield. 1H-NMR (CDCl3, 300 MHz) δ7.56 (1H, d, J=16.55 Hz), 7.37 (2H, d), 6.80 (2H, d), 6.22 (1H, d, J=16.55 Hz), 3.73 (3H, s), 3.70 (3H, s); 13C-NMR (CDCl3, 75.4 MHz) δ167.7, 161.4, 144.5, 129.7, 127.1, 115.2, 114.3, 55.3, 51.5.

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-3f10c52917e242f1b549d3d2b543a9fc
出典データセット
uspto-grants-2010_06
特許番号
US07741508B2

関連ノート

読み込み中…