Sulfuric Acid → 2-(Methoxycarbonyl)-6-nitrobenzoic acid

HRID 494344

Reaktionsgleichung

Reaktionsgleichung von HRID 494344
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14])([O-:3])=[O:2].[CH:16]([O-])([O-])OC.S(=O)(=O)(O)O>CO>[C:13]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH3:16])=[O:8])([OH:15])=[O:14]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 690433-Nitrophthalic acidHCID 53629101Methylorthoformate

Produkt 1

HCID 43994772-(Methoxycarbonyl)-6-nitrobenzoic acidAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of 3-nitrophthalic acid (211 g) and methyl orthoformate (127 g) in methanol (420 ml) was added conc. sulfuric acid (20 ml) dropwise with stirring. The reaction mixture was heated under reflux for 18 hours and concentrated to dryness. After addition of water (30 ml) to the residue, the mixture was stirred at 3-10° C. for one hour. The precipitated crystals were recrystallized from ethyl acetate-hexane to give pale yellow prisms (185 g, 82%), m.p. 166-168° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated to dryness
  4. additionAfter addition of water (30 ml) to the residue
  5. stirringthe mixture was stirred at 3-10° C. for one hour
  6. customThe precipitated crystals were recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-8f4c750e7b7c4431acc82c6ab7a7af32
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538133B2

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