Tetrahydrofuran → 2'-Hydroxy-4'-methoxyacetanilide

HRID 270057

Reaktionsgleichung

Reaktionsgleichung von HRID 270057
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[OH:12])([O-])=O.[H][H].C1C[O:18][CH2:17][CH2:16]1>[Pd]>[OH:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[NH:1][C:17](=[O:18])[CH3:16]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 2196355-Methoxy-2-nitrophenolHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 41051392'-Hydroxy-4'-methoxyacetanilideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-Nitro-5-methoxyphenol (prepared from 3-methoxyphenol, R. J. Maleski, Synthetic Communications, 1993, 23, 343-348) (48.5 g, 0.287 mol) dissolved in THF (1.5 L) was hydrogenated at ambient temperature over night with 10% palladium on carbon (10 g) until 20.3 L of hydrogen was consumed. After filtration and evaporation the residue was suspended in degased water (1.7 L) and acetic anhydride (42.5 mL) was added with stirring. The mixture was heated to 60° C. for 1 h and then cooled to room temperature. The volatiles were removed in vacuo and the solid was washed thoroughly with water and dried in vacuo to give brick-red crystals (41.7 g, 80%).

Aufarbeitung

  1. customwas consumed
  2. filtrationAfter filtration and evaporation the residue
  3. additionacetic anhydride (42.5 mL) was added
  4. temperaturecooled to room temperature
  5. customThe volatiles were removed in vacuo
  6. washthe solid was washed thoroughly with water
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9dc2eff7eedb4014bf7a9f83c185b290
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449475B2

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