Ethanol → 3'-Chloro-4'-methoxyacetophenone

HRID 343067

Reaction equation

HRID 343067 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([OH:7])[CH3:6].C(Cl)(=O)C.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20]>C(Cl)(Cl)Cl.O>[CH3:6][C:5]([C:17]1[CH:16]=[CH:15][C:14]([O:19][CH3:20])=[C:13]([Cl:12])[CH:18]=1)=[O:7]

Participants

7

Reactant 4

HCID 702EthanolHCID 6367Acetyl chlorideHCID 130112-ChloroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5208573'-Chloro-4'-methoxyacetophenoneYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

Anhydrous aluminum chloride (281 g, 2.104 mol) and 1 L of ethanol-free chloroform were maintained at 0° C. with an ice bath while a solution of acetyl chloride (162 g, 2.28 mol) in 300 mL of chloroform was added over 25 minutes. To this solution was added 2-chloroanisole (250 g, 1.75 mol) in 250 mL of chloroform over 1 hour. The solution was stirred at room temperature for 16 hours and was poured into a mixture of ice and water. The phases were separated and the aqueous phase was extracted with dichloromethane and combined with the original organic phase. The combined organics were dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford a solid which was crystallized from dichloromethane/hexane to give 3-chloro-4-methoxyacetophenone (246 g, 76%) which was used directly in the next step without further purification.

Workup

  1. additionwas added over 25 minutes
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organics were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a solid which
  8. customwas crystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-9411050bbca0425fa69676e3ac496baf
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Linked notes

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