Methanol → Methyl 2-methyl-5-nitrobenzoate

HRID 8913

Reaktionsgleichung

Reaktionsgleichung von HRID 8913
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[CH3:1]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5196832-Methyl-5-nitrobenzoic acid

Produkt 1

HCID 4377758Methyl 2-methyl-5-nitrobenzoateAusbeute 99 %

Versuchsvorschrift

A solution of 2-methyl-5-nitrobenzoic acid (1.51 g, 8.34 mmol) and H2SO4 (catalytic) in MeOH (20 mL) was heated at reflux for 17 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (40 mL), washed with saturated NaHCO3(aq) (30 mL), then dried (MgSO4) and concentrated in vacuo to give yellow crystals (1.62 g, 99%). 1H NMR (CDCl3) δ 2.72 (s, 3H), 3.96 (s, 3H), 7.44 (d, 1H, J=8.7 Hz), 8.24 (dd, 1H, J=8.7, 2.7 Hz), 8.78 (d, 1H, J=2.7 Hz).

Aufarbeitung

  1. temperatureat reflux for 17 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (40 mL)
  4. washwashed with saturated NaHCO3(aq) (30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7ea900c0e78d4c128d01976a5f4b69d7
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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