Hydrochloric Acid → 1-(3-Fluoro-4-methoxyphenyl)ethan-1-one

HRID 2118629Notes

Reaction equation

HRID 2118629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[C:10](Cl)(=[O:12])[CH3:11].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[CH3:11][C:10]([C:6]1[CH:5]=[CH:4][C:3]([O:8][CH3:9])=[C:2]([F:1])[CH:7]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 675762-FluoroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 968281-(3-Fluoro-4-methoxyphenyl)ethan-1-oneYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 26 grams (206 millimoles) of ortho-fluoroanisole and 19.4 grams (247 millimoles) of acetyl chloride was dissolved in 200 milliliters of methylene chloride, and then 33.0 grams (247 millimoles) of anhydrous aluminum chloride was gradually added thereto while cooling with ice and stirring. The resulting mixture was further stirred for 1.5 hours while cooling with ice. The reaction mixture was added to 1,200 milliliters of 5% hydrochloric acid, which was then allowed to separate into aqueous and organic layers. The organic layer thus obtained was washed with a 5% aqueous solution of sodium carbonate and dried over anhydrous sodium sulfate and, thereafter, the methylene chloride was distilled away under reduced pressure, and the residue was recrystallized from ethanol. Thus, as a product, 30.4 grams (181 millimoles) of 3-fluoro-4-methoxyacetophenone was obtained (yield, 88%).

Workup

  1. temperaturewhile cooling with ice
  2. stirringThe resulting mixture was further stirred for 1.5 hours
  3. temperaturewhile cooling with ice
  4. customto separate into aqueous and organic layers
  5. customThe organic layer thus obtained
  6. washwas washed with a 5% aqueous solution of sodium carbonate
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe methylene chloride was distilled away under reduced pressure
  9. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7f20f9eb6dc947e8a71074a5085bac93
Source dataset
uspto-grants-1987_07
Patent number
US04680054

Reaction notes

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