Water → HCID 21995779, compound

HRID 1978762Notes

Reaction equation

HRID 1978762 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](O)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[C:12](=[O:15])([O-])[O-].[K+].[K+].C[CH:19]([CH2:21]Br)C.[OH2:23].CN([CH:27]=[O:28])C>>[CH3:27][O:28][CH:19]([O:15][CH3:12])[CH2:21][O:23][CH2:3][CH2:2][CH2:1][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 29352Phenol, 4-propoxy-

Product 1

HCID 21995779HCID 21995779, compound

Procedure

To a suspension of 4-propoxyphenol (10.0 g) and potassium carbonate (10.0 g) in DMF (50 ml) was added bromoacetaldehydedimethylacetal (12.2 g), and the mixture was refluxed for 14 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, and the residue was purified with silica gel column chromatography to give yellow oil of 4-(2,2-dimethoxy)ethoxypropoxybenzene (12.2 g).

Workup

  1. temperaturethe mixture was refluxed for 14 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
  8. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-097729ea62d84fc4b7fe3e05f2ffd383
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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