2,3-Dimethylanisole → 2-Methoxy-6-methylbenzaldehyde

HRID 2036042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036042
S1(OS(=O)(=O)OOOO1)(=O)=O.[K].[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[O:21][CH3:22].C(OCC)(=[O:25])C.CCCCCC>O.C(#N)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:22][O:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[C:14]=1[CH:13]=[O:25]

Komponenten

6

Edukt 3

HCID 762692,3-DimethylanisoleHCID 21226206Ethyl acetate hexaneHCID 86652980Potassium peroxy disulphate

Produkt 1

HCID 6402382-Methoxy-6-methylbenzaldehydeAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

Potassium peroxy disulphate (89.31 g, 0.33 mol) and copper (II) sulphate pentahydrate (27.22 g, 0.11 mol) was added to a solution of 2,3-dimethylanisole (15 g, 0.11 mol) in acetonitrile water mixture (750 ml, 1:1). The reaction mixture was stirred for 15 min at reflux until no starting material remained as judged by TLC (Thin Layer Chromatography). On cooling the reaction mixture to room temperature, the product was extracted into dichloromethane (2×225 ml). The organic layer was washed with water (2×100 ml) and brine solution (100 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product. Column chromatography using 4/96 ethyl acetate/hexane yielded 2-Methoxy-6-methylbenzaldehyde (7.32 g, 44.2%).

Aufarbeitung

  1. temperatureat reflux until no starting material
  2. extractionthe product was extracted into dichloromethane (2×225 ml)
  3. washThe organic layer was washed with water (2×100 ml) and brine solution (100 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product

Quellen und Nachweise

ORD-Eintrag
ord-2d879bee0a704ed7b2f08809380094d4
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575161B2

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