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

HRID 638711

반응식

HRID 638711 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+].[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9fe5ecc39f934331aa93e1d1dc3ab976
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691364B2

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