Methanol → 4-Methoxy-3,5-dinitrobenzoic acid

HRID 852533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852533
[OH-:1].[K+].Cl[C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:16]([O-:18])=[O:17].[CH3:19]O>O>[CH3:19][O:1][C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:16]([O-:18])=[O:17]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 83774-Chloro-3,5-dinitrobenzoic acidHCID 14797Potassium Hydroxide2×

Produkt 1

HCID 2916454-Methoxy-3,5-dinitrobenzoic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of KOH (1.12 g, 20 mmol, 1 equiv) in MeOH (20 ml) at 0° C. was added portionwise 4-chloro-3,5-dinitrobenzoic acid (D23) (4.93 g, 20 mmol, 1 equiv). The resulting mixture was refluxed for 1 h then cooled to room temperature. A second portion of KOH (1.12 g, 20 mmol, 1 equiv) was added and the mixture refluxed for 90 min, cooled to room temperature and diluted with H2O. The aqueous phase was acidified to pH 1 and extracted with AcOEt. The organic phase was dried over MgSO4 and concentrated in vacuo to give crude 4-methoxy-3,5-dinitro-benzoic acid (D24) (4.49 g, 93%) as a light brown solid.

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 1 h
  2. temperaturethe mixture refluxed for 90 min
  3. temperaturecooled to room temperature
  4. extractionextracted with AcOEt
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5983826bf1fa4794b588b739d5b207e9
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

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