Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 638705

반응식

HRID 638705 반응식
[NH:1]([C:5]1[CH:11]=[CH:10][C:8]([OH:9])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1)[CH3:24]

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

To a mixture of Paracetamol (300 g, 1.984 mol), and anhydrous K2CO3 (1.80 Kg, 7.814 mmol) in anhydrous acetone (3 liters) was added ethyl bromoacetate (452 gr, 2.7 mol) and refluxed for 16 hours. Acetone was distilled off and water (5 liter) was added. Crude 13 was filtered, dried and recrystallised from a mixture of toluene:hexane (1:5) to give pure 13 (377 g, 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 off
  3. additionwater (5 liter) was added
  4. filtrationCrude 13 was filtered
  5. customdried
  6. customrecrystallised from a mixture of toluene:hexane (1:5)

출처 및 근거

ORD 기록
ord-034d4d086e5c4ec694ca59999af611f7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691364B2

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