Water → 1,5-Bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one

HRID 1085628

반응식

HRID 1085628 반응식
[I-].C[N+]([CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=1)=O)(C)C.[C:22]([O:25][CH2:26][CH3:27])(=O)C.[OH2:28]>>[CH3:21][O:20][C:12]1[CH:11]=[C:10]([CH:8]=[CH:7][C:6]([CH:7]=[CH:8][C:10]2[CH:27]=[C:26]([O:25][CH3:22])[C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=2)=[O:28])[CH:15]=[C:14]([O:16][CH3:17])[C:13]=1[O:18][CH3:19]

참가 물질

4

반응물 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 104092223-(N,N,N-trimethylammonio)-1-(3,4,5-trimethoxyphenyl)propan-1-one iodide

생성물 1

HCID 3834051,5-Bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one

실험 절차

3-(N,N,N-trimethylammonio)-1-(3,4,5-trimethoxyphenyl)propan-1-one iodide (355.9 g, 0.87 mole) was suspended in a mixture of water (3.56 L) and of ethyl acetate (2.54 L) and refluxed with rapid stirring for 2-3 hours. The mixture was cooled and the pale yellow organic layer was removed. Fresh ethyl acetate (2 L) was added and the mixture was refluxed for 1 hour, and the process was repeated once again. The organic layers were combined, washed with brine, dried over anhydrous MgSO4, and evaporated to dryness to provide a yellow oil, which was crystallized from hexane/ether to give 3,4,5-trimethoxyphenylvinyl ketone (m.p. 45°-47° C.). 200 MHz 1H NMR (CDCl3): δ 3.94 (9H, s, 3 OCH3), 5.92 (1H, dd, J=1.5 Hz, J=9 Hz), 6.44 (1H, dd, J=1.5 Hz, J=1.5 Hz, J=16 Hz), 7.18 (1H, dd, J=16 Hz, J=9 Hz), 7.28 (2H, H2 and H6).

후처리

  1. temperaturerefluxed
  2. temperatureThe mixture was cooled
  3. customthe pale yellow organic layer was removed
  4. additionFresh ethyl acetate (2 L) was added
  5. temperaturethe mixture was refluxed for 1 hour
  6. washwashed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. customevaporated to dryness
  9. customto provide a yellow oil, which
  10. customwas crystallized from hexane/ether

출처 및 근거

ORD 기록
ord-1d344d6e311a4bccb1db48ae8e8a97d1
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05010100

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