5-(Benzyloxy)-1,3-dimethyl-2-nitrobenzene → 4-Benzyloxy-2,6-dimethylaniline

HRID 1154001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1154001
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:19])[C:12]([N+:16]([O-])=O)=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([NH2:16])=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 133699565-(Benzyloxy)-1,3-dimethyl-2-nitrobenzene

Produkt 1

HCID 133699574-Benzyloxy-2,6-dimethylanilineAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Zinc dust is added to a solution of 5-benzyloxy-2-nitro-m-xylene (22.9 g) in 250 ml of glacial acetic acid. The reaction mixture is stirred until the solution is colorless. The reaction mixture is cooled, filtered through celite to remove excess zinc and the filtrate diluted with H2O and cooled with ice. NH3 is added to make the solution slightly alkaline followed by a small amount of sodium hydrosulfite. The product is filtered, dissolved in methylene chloride, dried and concentrated to give 18.3 grams of a tan solid.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered through celite
  3. customto remove excess zinc
  4. additionthe filtrate diluted with H2O
  5. temperaturecooled with ice
  6. additionNH3 is added
  7. filtrationThe product is filtered
  8. dissolutiondissolved in methylene chloride
  9. customdried
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3dd0aa44010d4c19a9704ceb985a9028
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04487779

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