Ammonia → 1-(5-Fluoro-2-methoxyphenyl)ethan-1-one

HRID 1413855

Reaction equation

HRID 1413855 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[CH3:8][C:9]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1O)=[O:10].C(=O)([O-])[O-].[K+].[K+].N>CC(C)=O>[CH3:8][C:9]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[O:6][CH3:7])=[O:10]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 959922-Acetyl-4-fluorophenol

Product 1

HCID 27373561-(5-Fluoro-2-methoxyphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dimethyl sulphate (30 ml) was added dropwise over 45 min to a stirred mixture of 5-fluoro-2-hydroxyacetophenone (32.43 g) and potassium carbonate (40.5 g) in acetone (500 ml) and the mixture was then heated under reflux for 8 hr. Concentrated ammonia solution was added and the inorganic solids removed by filtration. The solvent was removed under reduced pressure and the product was dissolved in ether and washed with water. After drying the ethereal solution (Na2SO4) the ether was removed under reduced pressure and the residue was distilled to give 5-fluoro-2-methoxyacetophenone (28.4 g); b.p. 58°-64 ° C./0.2 mm.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux for 8 hr
  3. customthe inorganic solids removed by filtration
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe product was dissolved in ether
  6. washwashed with water
  7. dry with materialAfter drying the ethereal solution (Na2SO4) the ether
  8. customwas removed under reduced pressure
  9. distillationthe residue was distilled

Sources & evidence

ORD record
ord-de0940015fd3448eb659129b61187bd2
Source dataset
uspto-grants-1981_02
Patent number
US04251546

Linked notes

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