Potassium methoxide → 3-Methoxy-2-methyl-6-nitro-benzoic acid

HRID 604282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604282
F[C:2]1[C:3]([CH3:14])=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:15][O-:16].[K+]>C1COCC1.CO>[CH3:15][O:16][C:2]1[C:3]([CH3:14])=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 2

HCID 23664618Potassium methoxideHCID 509149483-Fluoro-2-methyl-6-nitrobenzoic acid

Produkt 1

HCID 598492163-Methoxy-2-methyl-6-nitro-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirring solution of 3-Fluoro-2-methyl-6-nitro-benzoic acid (4.2 g, 21 mmol) in THF (40 mL) and methanol (40 mL) is added potassium methoxide in methanol (15 g, 63 mmol) and the solution is heated to 100° C. for 2 hours. The reaction mixture is cooled to room temperature and then the mixture is quenched with a 1N HCl solution and partitioned between ethyl acetate. The organic layer is washed with brine and then concentrated to give 3-Methoxy-2-methyl-6-nitro-benzoic acid (4.3 g) in quantitative yields. 1H-NMR (400 MHz, δ, ppm) CDCl3: 2.32 (s, 3H), 3.98 (s, 3H), 6.95 (d, 1H), 8.15 (d, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe mixture is quenched with a 1N HCl solution
  3. custompartitioned between ethyl acetate
  4. washThe organic layer is washed with brine
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3f209a146c5b445d80373c9e577888c9
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910585B2

Notizen zur Reaktion

Wird geladen…