Methanol → Methyl 2-ethoxy-4,5-dinitrobenzoate

HRID 1012125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012125
S(Cl)(Cl)=O.[N+:5]([C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([O:20][CH2:21][CH3:22])[CH:9]=1)([O-:7])=[O:6].[CH3:23]O>>[CH3:23][O:13][C:12](=[O:14])[C:11]1[CH:15]=[C:16]([N+:17]([O-:19])=[O:18])[C:8]([N+:5]([O-:7])=[O:6])=[CH:9][C:10]=1[O:20][CH2:21][CH3:22]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 858173894,5-dinitro-2-ethoxy-benzoic Acid

Produkt 1

HCID 71418202Methyl 2-ethoxy-4,5-dinitrobenzoate

Versuchsvorschrift

Thionyl chloride (315 μl, 4.30 mmol) was slowly added to a mixture of 4,5-dinitro-2-ethoxy-benzoic acid (1.00 g, 3.91 mmol) in methanol (10 mL) at r.t. The mixture was stirred for 16 h, then reduced in vacuo azeotroping with toluene. The residue was then purified by column chromatography using P.E.-EtOAc (1:0-1:1) to give the title compound (606 mg) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1H), 8.00 (s, 1H), 4.35 (q, 2H), 3.85 (s, 3H), 1.35 (t, 3H).

Aufarbeitung

  1. customazeotroping with toluene
  2. customThe residue was then purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ce0fe3637ff34fada82e46e16fba09fb
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977477B2

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