Acetyl chloride → 4-[(8-Acetyl-7-hydroxy-2-naphthalenyl)oxy]butanoic acid methyl ester

HRID 1719418노트

반응식

HRID 1719418 반응식
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:9][O:10][C:11](=[O:27])[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][C:20]([OH:26])=[CH:21][CH:22]=2)[CH:17]=1>ClC(Cl)C>[CH3:9][O:10][C:11](=[O:27])[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[C:19]([C:1](=[O:3])[CH3:2])[C:20]([OH:26])=[CH:21][CH:22]=2)[CH:17]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 135047814-[(7-Hydroxy-2-naphthalenyl)oxy]butanoic acid methyl ester

생성물 1

HCID 544071994-[(8-Acetyl-7-hydroxy-2-naphthalenyl)oxy]butanoic acid methyl ester수율 29%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

Under argon, 2.8 ml of acetyl chloride was added to a suspension of 5.15 g of aluminum chloride in 120 ml of dichloroethane and then 8 g of 4-[(7-hydroxy-2-naphthalenyl)oxy] butanoic acid methyl ester was added. The resulting mixture was stirred at room temperature for 30 minutes and at reflux for 16 hours. The solution was filtered and the dark residue was broken up with 3N hydrochloric acid and extracted with methylene chloride. The filtrate was combined with the methylene chloride extract, washed and dried to give a black oil which was purified by high pressure liquid chromatography, eluting with 2% ethyl acetate/toluene to yield 2.72 g, (29%) of 4-[(8-acetyl-7-hydroxy-2-naphthalenyl)oxy] butanoic acid methyl ester as an oil.

후처리

  1. temperatureat reflux for 16 hours
  2. filtrationThe solution was filtered
  3. extractionextracted with methylene chloride
  4. extractionextract
  5. washwashed
  6. customdried
  7. customto give a black oil which
  8. customwas purified by high pressure liquid chromatography
  9. washeluting with 2% ethyl acetate/toluene

출처 및 근거

ORD 기록
ord-f5a421ef01d44e6da9cb935c11895ebb
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539419

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