Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 638705

反応式

HRID 638705 の反応式
[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]

参加物

5

反応物 3

HCID 1983AcetaminophenHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

生成物 1

HCID 309738Ethyl 2-(4-acetamidophenoxy)acetate収率 80.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-034d4d086e5c4ec694ca59999af611f7
出典データセット
uspto-grants-2010_04
特許番号
US07691364B2

関連ノート

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