tert-Butanol → 2-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

HRID 481373노트

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HRID 481373 반응식
[OH:1][C:2]([CH3:14])([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8](SC)=[CH:7][CH:6]=1)=[O:4].O[O:16][S:17]([O-:19])=O.[K+].[C:21](O)(C)(C)C>C(Cl)Cl.O.CCOC(C)=O>[OH:1][C:2]([CH3:13])([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:17]([CH3:21])(=[O:19])=[O:16])=[CH:7][CH:6]=1)=[O:4]

참가 물질

7

반응물 3

HCID 6386tert-ButanolHCID 114131682-Hydroxy-4'(methylthio)isobutyrophenoneHCID 23707502Potassium hydroxy sulfite

생성물 1

HCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a cold (4° C.) solution of 2-hydroxy-2-methyl-1 -(4-(methylthio) phenyl)propan-1-one (45.0 g, 214 mmol, Step 2) in t-butanol (500 mL) and CH2Cl2 (500 mL) was added a solution of OXONE™ (194 g, 316 mmol) in water (1.4 L). The resulting suspension was stirred at r.t. for 18 h. The reaction was diluted with EtOAc (400 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2×250 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude product was dissolved in diethyl ether (250 mL), hexane was added (150 mL) and the product was swished for 2 h. The product was collected by filtration to give the title compound as a yellow solid.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with EtOAc (2×250 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude product was dissolved in diethyl ether (250 mL)
  6. additionhexane was added (150 mL)
  7. waitthe product was swished for 2 h
  8. filtrationThe product was collected by filtration

출처 및 근거

ORD 기록
ord-48d9e9d698e143f3b53abaac115c3710
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789413

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