Methanol → Methyl 2,4,5-trimethoxycinnamate

HRID 18907노트

반응식

HRID 18907 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:4]=1[CH:5]=[CH:6][CH:7]=[O:8].C(C1C(=O)C(Cl)=C(Cl)[C:21](=[O:22])C=1C#N)#N.CO>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:4]=1[CH:5]=[CH:6][C:7]([O:22][CH3:21])=[O:8]

참가 물질

5

반응물 3

HCID 887MethanolHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 540454412,4,5-Trimethoxy cinnamaldehyde

생성물 1

HCID 68740423Methyl 2,4,5-trimethoxycinnamate수율 84%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A homogeneous mixture containing 2,4,5-trimethoxycinnamaldehyde (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 120 (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 2,4,5-trimethoxycinnamate (from formula I where X1═OCH3, X2═H, X3═OCH3, X4═OCH3, X5═H, R═CH3) is isolated in 84% yield. 1H-NMR (CDCl3, 300 MHz) δ7.91 (1H, d, J=16.10 Hz), 7.01 (1H, s), 6.50 (1H, s), 6.37 (1H, d, J=16.10 Hz), 3.93 (3H, s), 3.88 (3H, s), 3.87 (3H, s), 3.80 (3H, s); 13C-NMR (CDCl3, 75.4 MHz) δ168.2, 153.9, 151.9, 143.4, 139.7, 116.6, 115.4, 112.6, 96.9, 56.5, 56.4, 56.1, 51.5.

후처리

  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

출처 및 근거

ORD 기록
ord-5ee91a5a672f4d81acfe2c02704491b1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741508B2

반응 노트

불러오는 중…