Dimethyl Sulfate → 4'-Methoxyacetophenone

HRID 37479Notes

Reaction equation

HRID 37479 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[OH-].[Na+].S(OC)(O[CH3:17])(=O)=O>C(O)C.O>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:17])=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 74694'-HydroxyacetophenoneHCID 14798Sodium Hydroxide2×

Product 1

HCID 74764'-Methoxyacetophenone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In 200 ml of ethanol was dissolved 30.0 g of 4-hydroxyacetophenone, and a solution of 11.3 g (1.28 eq.) of sodium hydroxide in 60 ml of water and 33.9 g (1.22 eq.) of dimethyl sulfate were added dropwise consecutively. After the reaction mixture was refluxed for 30 minutes', a solution of 2.8 g (0.32 eq.) of sodium hydroxide dissolved in 10 ml of water was added, followed by heating under for 3 hours' reflux. After the solvent was distilled off, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried. Then, the solvent was distilled off. The resulting crystals were collected by filtration with hexane.

Workup

  1. additionwas added
  2. temperatureby heating under for 3 hours'
  3. temperaturereflux
  4. distillationAfter the solvent was distilled off
  5. additionwater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride, and dried
  9. distillationThen, the solvent was distilled off
  10. filtrationThe resulting crystals were collected by filtration with hexane

Sources & evidence

ORD record
ord-1fa002c8beb44fb8ac4d389aa5ae8184
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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