3,4-Dimethoxy-2-nitrobenzaldehyde → 3,4-dimethoxy-2-nitrobenzoic acid

HRID 354830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354830
[Mn]([O-])(=O)(=O)=[O:2].[K+].[CH3:7][O:8][C:9]1[C:10]([N+:19]([O-:21])=[O:20])=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=[O:13]>O.CC(C)=O>[CH3:7][O:8][C:9]1[C:10]([N+:19]([O-:21])=[O:20])=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:12]([OH:2])=[O:13]

Komponenten

5

Edukt 2

HCID 1524373,4-Dimethoxy-2-nitrobenzaldehydeHCID 516875Potassium Permanganate

Produkt 1

HCID 12522693,4-dimethoxy-2-nitrobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 823 g. potassium permanganate in about 8.5 liters of H2O was gradually added to a refluxing solution of 3,4-dimethoxy-2-nitrobenzaldehyde (550 g., 2.60 moles) in 5.6 liters of acetone. The reaction mixture was refluxed for four more hours, then filtered through diatomaceous earth while hot and the filter cake washed with hot water. The acetone was removed in vacuo and a small amount of unreacted solid was filtered off. The aqueous solution was acidified with 2 N hydrochloric acid (1.8 liters) to yield 505 g. (85%) of the essentially pure title compound. Recrystallization from water afforded colorless crystals, M.P. 200°-202° C.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for four more hours
  2. filtrationfiltered through diatomaceous earth while hot and the filter cake
  3. washwashed with hot water
  4. customThe acetone was removed in vacuo
  5. filtrationa small amount of unreacted solid was filtered off
  6. customto yield 505 g

Quellen und Nachweise

ORD-Eintrag
ord-c89542a8b66644d794bcd35d8acb4497
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377581

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