Water → p-(2,2-Dimethoxyethoxy)anisole

HRID 1978764Notes

Reaction equation

HRID 1978764 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].C[CH:17]([CH2:19]Br)C.O.CN([CH:25]=[O:26])C>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:19][CH:17]([O:13][CH3:10])[O:26][CH3:25])=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 65551-Bromo-2-methylpropaneHCID 90154-MethoxyphenolHCID 11430Potassium Carbonate

Product 1

HCID 110244p-(2,2-Dimethoxyethoxy)anisole

Procedure

To a suspension of 4-methoxyphenol (26.7 g) and potassium carbonate (32.8 g) in DMF (150 ml) was added bromoacetaldehydedimethylacetal (40.1 g), and the mixture was refluxed for 2.5 hours and cooled. To the mixture was added water, and the mixture was extracted with ethyl acetate (twice). The organic layer was washed with 1N sodium hydroxide solution (twice) and then washed with saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give dark brown oil of 4-methoxy-(2,2-dimethoxy)ethoxybenzene (40.4 g).

Workup

  1. temperaturethe mixture was refluxed for 2.5 hours
  2. temperaturecooled
  3. extractionthe mixture was extracted with ethyl acetate (twice)
  4. washThe organic layer was washed with 1N sodium hydroxide solution (twice) and
  5. washthen washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-4a973842de544bfcb602e231db9db41d
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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