Acetaminophen → 6-(4-Acetylaminophenoxy)-hexanoic acid methyl ester

HRID 638711

反応式

HRID 638711 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+].[I-].[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]>CC(C)=O>[CH3:29][O:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 1983AcetaminophenHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 4170292Methyl 6-Bromohexanoate

生成物 1

HCID 497644916-(4-Acetylaminophenoxy)-hexanoic acid methyl ester収率 66%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a mixture of Paracetamol (250 g, 1.654 mol), anhydrous K2CO3 (800 g, 5.789 mol) and sodium iodide (17 g, 113 mmol) in anhydrous acetone (5 liters) was added methyl 6-bromohexanoate (470 g, 2.25 mol) and refluxed for 60 hours. Acetone was distilled off and water (3 liter) was added. Crude 19 was filtered, dried and recrystallised from a mixture of chloroform:hexane (1:5) to give pure 19 (195 g, 66%) as a white powder. The melting point was found to be 96.4-98.8° C. The product was tested by HPLC and found to be 99%+ pure. The structure was confirmed with NMR.

後処理

  1. temperaturerefluxed for 60 hours
  2. distillationAcetone was distilled off
  3. additionwater (3 liter) was added
  4. filtrationCrude 19 was filtered
  5. customdried
  6. customrecrystallised from a mixture of chloroform:hexane (1:5)

出典と根拠

ORDレコード
ord-9fe5ecc39f934331aa93e1d1dc3ab976
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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