Diethyl Ether → 3,5-Dimethoxystyrene

HRID 1003948Notes

Reaction equation

HRID 1003948 reaction equation
[C:1](Cl)(=O)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH:10]=O.[Cl-].[NH4+].C(OCC)C>CN(C)C=O.BrCBr.[Zn]>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH:10]=[CH2:1]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 25517Ammonium ChlorideHCID 817473,5-Dimethoxybenzaldehyde

Product 1

HCID 98152983,5-DimethoxystyreneYield 373.9%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 3024DibromomethaneSolventHCID 6228DimethylformamideSolvent

Procedure

Zinc powder (purity; 85%, 14.75 g) is suspended in N,N-dimethylformamide (50 ml) under argon atmosphere, and thereto is added dropwise with stirring acetyl chloride (1.06 g) at 50° C. over a period of 10 minutes, and then the mixture is stirred for 15 minutes. To the mixture is added dropwise a solution of 3,5-dimethoxybenzaldehyde (10 g) in dibromomethane (15.69 g) over a period of 20 minutes, and the mixture is stirred for 30 minutes. The reaction solution is cooled with ice, and thereto is added dropwise a saturated aqueous ammonium chloride solution (40 ml), and further thereto is added diethyl ether. The insoluble materials are removed by filtration, and the filtrate is extracted with diethyl ether. The extract is washed successively with 10% hydrochloric acid, water, 10% aqueous sodium hydroxide solution, and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure to give 3,5-dimethoxystyrene (8.29 g).

Workup

  1. stirringthe mixture is stirred for 30 minutes
  2. temperatureThe reaction solution is cooled with ice
  3. customThe insoluble materials are removed by filtration
  4. extractionthe filtrate is extracted with diethyl ether
  5. washThe extract is washed successively with 10% hydrochloric acid, water, 10% aqueous sodium hydroxide solution
  6. dry with materiala saturated aqueous sodium chloride solution, dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d6d6a0d208a45b2ae7e996ab9b18811
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Reaction notes

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