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

HRID 1602550

Reaktionsgleichung

Reaktionsgleichung von HRID 1602550
[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]

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 1140TolueneLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3e2c4c6d1dba48529d062a001a266ed7
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05981576

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