Sodium Hydroxide → 2-Hydroxy-2-methyl-1-[4-(methylthio)phenyl]-1-butanone

HRID 565123

반응식

HRID 565123 반응식
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH:10]([CH3:13])[CH2:11][CH3:12])=[CH:5][CH:4]=1.[OH-:15].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[OH:15][C:10]([CH3:13])([CH2:11][CH3:12])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1)=[O:14]

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 154806432-Methyl-1-[4-(methylthio)phenyl]-1-butanone

생성물 1

HCID 101307312-Hydroxy-2-methyl-1-[4-(methylthio)phenyl]-1-butanone

시약·촉매·용매 3

HCID 21218Trioctylmethylammonium chloride촉매HCID 1140Toluene용매HCID 5943Carbon Tetrachloride용매

실험 절차

To a mixture of the ketone from Step 1 (10 g, 48 mmol) and Aliquat® 336 (20 mL) in CCl4 (40 mL) and toluene (80 mL) at r.t. was added NaOH pellets (3.8 g, 96 mmol). While stirring vigourously, the mixture was heated briefly to reflux and was then stirred overnight at r.t. After partitioning between CH2Cl2 and H2O, the whole was filtered through celite. The organic layer was dried (MgSO4), filtered, and evaporated. The residue was purified by flash chromatography (1:10 EtOAc: hexane) to give the title compound as a syrup (5.5 g).

후처리

  1. temperaturethe mixture was heated briefly
  2. temperatureto reflux
  3. stirringwas then stirred overnight at r.t
  4. customAfter partitioning between CH2Cl2 and H2O
  5. filtrationthe whole was filtered through celite
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (1:10 EtOAc: hexane)

출처 및 근거

ORD 기록
ord-95d67e736c114d7395561c7f451c366d
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169188A

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