Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 501829

반응식

HRID 501829 반응식
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:8]([C:12]1[CH:18]=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=1)[C:9]([CH3:11])=[O:10].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:16][C:15]1[CH:14]=[CH:13][C:12]([NH:8][C:9](=[O:10])[CH3:11])=[CH:18][CH:17]=1)[CH3:7]

참가 물질

5

반응물 3

HCID 1983AcetaminophenHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

생성물 1

HCID 309738Ethyl 2-(4-acetamidophenoxy)acetate수율 80.1%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Ethyl bromoacetate (452 g, 2.7 mol.) was added to a mixture of paracetamol (300 g, 1.984 mol) and anhydrous K2CO3 (1.80 kg, 7.814 mmol) in anhydrous acetone (3 L) and refluxed for 16 hours. Acetone was distilled and water (5 L) was added. Crude 1 was filtered, dried and recrystallised from a mixture of toluene:hexane (1:5) to give pure 1 (377 grams, 80%) as a white shining powder. The melting point was found to be 104.2-106.2° C.

후처리

  1. temperaturerefluxed for 16 hours
  2. distillationAcetone was distilled
  3. additionwater (5 L) was added
  4. filtrationCrude 1 was filtered
  5. customdried
  6. customrecrystallised from a mixture of toluene:hexane (1:5)

출처 및 근거

ORD 기록
ord-825db2fc7c074559b6cc349432834b82
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772352B2

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