Methanol → 4-Methoxy-2,5-dimethylaniline

HRID 985592

Reaktionsgleichung

Reaktionsgleichung von HRID 985592
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-])=O.[CH3:12][OH:13]>S(=O)(=O)(O)O.[Pd]>[CH3:12][O:13][C:6]1[C:5]([CH3:8])=[CH:4][C:3]([NH2:9])=[C:2]([CH3:1])[CH:7]=1

Komponenten

5

Edukt 2

HCID 887MethanolHCID 6974Nitro-p-xylene

Produkt 1

HCID 225068644-Methoxy-2,5-dimethylanilineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

2,5-Dimethylnitrobenzene, (46.8 ml, 0.35 mol) was dissolved in sulfuric acid (47.1 ml)/methanol (650 ml) and then 5% palladium on carbon (50% hydrate, 0.35 g) was added. The mixture was allowed to react for 3 hours under hydrogen atmosphere at the pressure of 5 atms at 40° C. After cooling, the catalyst was removed, and methanol was removed under reduced pressure. The residue was poured into a 25% aqueous ammonia solution with cooling on ice, and extracted with toluene. The extract was washed with 5% sodium hydrosulfite, dried over sodium sulfate and purified by column chromatography on a small amount of silica gel (toluene:ethyl acetate=1:1). The solvent was removed under reduced pressure and crystallization from hexane yielded 35.0 g of the title compound.

Aufarbeitung

  1. customto react for 3 hours under hydrogen atmosphere at the pressure of 5 atms at 40° C
  2. temperatureAfter cooling
  3. customthe catalyst was removed
  4. custommethanol was removed under reduced pressure
  5. additionThe residue was poured into a 25% aqueous ammonia solution
  6. temperaturewith cooling on ice
  7. extractionextracted with toluene
  8. washThe extract was washed with 5% sodium hydrosulfite
  9. dry with materialdried over sodium sulfate
  10. custompurified by column chromatography on a small amount of silica gel (toluene:ethyl acetate=1:1)
  11. customThe solvent was removed under reduced pressure and crystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-3f191aabf4964fb4955f8af0be19d72b
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06872718B1

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