Ethanol → 3'-Chloro-4'-methoxyacetophenone

HRID 343067

반응식

HRID 343067 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9411050bbca0425fa69676e3ac496baf
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859257

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