Veratraldehyde → 3,4-Dimethoxystyrene

HRID 428715

Reaction equation

HRID 428715 reaction equation
[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]

Participants

5

Reactant 2

HCID 8419VeratraldehydeHCID 178418339Butyllithium

Product 1

HCID 614003,4-Dimethoxystyrene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e3ce95716b944a00b0556b5d224ca6bc
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Linked notes

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