Veratraldehyde → 3,4-Dimethoxystyrene

HRID 428715

反応式

HRID 428715 の反応式
[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]

参加物

5

反応物 2

HCID 8419VeratraldehydeHCID 178418339Butyllithium

生成物 1

HCID 614003,4-Dimethoxystyrene

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e3ce95716b944a00b0556b5d224ca6bc
出典データセット
uspto-grants-2001_11
特許番号
US06313310B1

関連ノート

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