Veratraldehyde → 3,4-Dimethoxystyrene

HRID 428715

반응식

HRID 428715 반응식
[CH2:1]([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH:11]=O>CCOCC.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][O:16][C:15]1[CH:14]=[CH:13][C:10]([CH:11]=[CH2:1])=[CH:9][C:8]=1[O:7][CH3:6]

참가 물질

5

반응물 2

HCID 8419VeratraldehydeHCID 178418339Butyllithium

생성물 1

HCID 614003,4-Dimethoxystyrene

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 3283Diethyl Ether용매

실험 절차

To a stirred solution of n-butyllithium (4 mL, 2,5 M solution in hexane, 10 mmol) (Aldrich) in ether (30 mL) was added methyltriphenylphosphonium bromide (3.57 g, 10 mmol) (Aldrich) over a period of 5 min. The reaction mixture was stirred for 4 h at room temperature. To the resulting orange solution was added 3,4-dimethoxybenzaldehyde (1.82 g, 11 mmol) (Aldrich) dropwise. The solution became colorless, and a white precipitate separated. The mixture was then heated to reflux and immediately allowed to cool to room temperature. The precipitate was removed by filtration. The precipitate was washed with ether and the combined ethereal filtrates were washed with water until neutral and then dried over anhydrous MgSO4. The solvent was removed and the residue, 1,2-dimethoxy-4-ethenyl -benzene, was used in the next reaction without further purification.

후처리

  1. customa white precipitate separated
  2. temperatureThe mixture was then heated
  3. temperatureto reflux
  4. temperatureto cool to room temperature
  5. customThe precipitate was removed by filtration
  6. washThe precipitate was washed with ether
  7. washthe combined ethereal filtrates were washed with water until neutral and
  8. dry with materialthen dried over anhydrous MgSO4
  9. customThe solvent was removed
  10. customthe residue, 1,2-dimethoxy-4-ethenyl -benzene, was used in the next reaction without further purification

출처 및 근거

ORD 기록
ord-e3ce95716b944a00b0556b5d224ca6bc
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313310B1

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