Veratraldehyde → 3,4-Dimethoxystyrene

HRID 428715

Reaktionsgleichung

Reaktionsgleichung von HRID 428715
[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]

Komponenten

5

Edukt 2

HCID 8419VeratraldehydeHCID 178418339Butyllithium

Produkt 1

HCID 614003,4-Dimethoxystyrene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e3ce95716b944a00b0556b5d224ca6bc
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313310B1

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