Hydrochloric Acid → 3'-Chloro-4'-methoxyacetophenone

HRID 2118626Notes

Reaction equation

HRID 2118626 reaction equation
[Cl: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]([Cl:1])[CH:7]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 130112-ChloroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5208573'-Chloro-4'-methoxyacetophenoneYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 30 grams (210 millimoles) of orthochloroanisole and 19.8 grams (252 millimoles) of acetyl chloride was dissolved in 400 milliliters of methylene chloride, and then 33.6 grams (252 millimoles) of anhydrous aluminum chloride was gradually added thereto while cooling with ice and stirring. The resulting mixture was further stirred for 3 hours while cooling with ice. The reaction mixture was allowed to stand to room temperature and stirred for 2 hours at room temperature. Then 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. Thus, as a product, 37.4 grams (202 millimoles) of 3-chloro-4-methoxyacetophenone was obtained (yield, 97%).

Workup

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

Sources & evidence

ORD record
ord-84945a5b92fd4e959745b61eeb56a838
Source dataset
uspto-grants-1987_07
Patent number
US04680054

Reaction notes

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