Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 501829

反応式

HRID 501829 の反応式
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]

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

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.

後処理

  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)

出典と根拠

ORDレコード
ord-825db2fc7c074559b6cc349432834b82
出典データセット
uspto-grants-2010_08
特許番号
US07772352B2

関連ノート

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