Hydrogen Peroxide → 4-(Methylsulfinyl)phenol

HRID 606364

Reaktionsgleichung

Reaktionsgleichung von HRID 606364
[OH-:1].[Na+].[CH3:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[OH:12]O.[OH:14]S([O-])=O.[Na+]>O.C(Cl)Cl>[CH3:3][S:4]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:14].[CH3:3][S:4]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:12])=[O:1]

Komponenten

8

Edukt 4

HCID 784Hydrogen PeroxideHCID 140864-(Methylthio)phenolHCID 14798Sodium HydroxideHCID 23665763Sodium Bisulfite

Produkt 2

HCID 1233504-(Methylsulfonyl)phenolAusbeute 30 %HCID 1519364-(Methylsulfinyl)phenolAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

H2WO4 (0.029 g, 0.114 mmol) was stirred in H2O (10 ml). 50% NaOH (0.040 ml) was first added (pH>12) and then ACOH (0.040 ml) to reach pH 5. 4-methylsulfanyl-phenol (4 g, 0.029 mol) was added and the reaction mixture was heated to 65° C. 30% H2O2 in H2O (3 ml) was added in portions over 10 minutes. The reaction mixture was allowed to stir at room temperature for 1 h. 50% NaHSO3 was added to quench the reaction. Methylene chloride was added and the compound was washed with brine and purified by chromatography (0→10% EtOH in methylene chloride) to give 1.9 g of 4-methanesulfinyl-phenol (1) (42%) and 1.5 g of 4-methanesulfonyl-phenol (2) (30%).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. washthe compound was washed with brine
  4. custompurified by chromatography (0→10% EtOH in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-f5776f7b9372442dadd73c095ea2ab1e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915295B2

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