Methanol → Methyl 3-(2,4-dinitrophenyl)-2-methylpropanoate

HRID 1038851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038851
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])([O-:3])=[O:2].OS(O)(=O)=O.[CH3:24]O>>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH:14]([CH3:18])[C:15]([O:17][CH3:24])=[O:16])([O-:3])=[O:2]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 662222213-(2,4-Dinitrophenyl)-2-methylpropanoic acid

Produkt 1

HCID 86665113Methyl 3-(2,4-dinitrophenyl)-2-methylpropanoateAusbeute 81 %

Versuchsvorschrift

To a solution of 3-(2,4-dinitrophenyl)-2-methylpropanoic acid (1.6 g, 5.0 mmol) in MeOH (10 mL) was added H2SO4 (0.85 mL, 16 mmol) and the mixture was heated to reflux overnight. The solvent was removed under reduced pressure and the residue was dissolved in DCM (100 mL). The organic solution was washed with saturated aqueous NaHCO3 and the layers were separated. The organic solution was dried over anhydrous Na2SO4 and filtered. The organic solution was directly purified by preparative TLC (1.0 mm plate), eluting with 5:1 pet ether/EtOAc to give methyl 3-(2,4-dinitrophenyl)-2-methylpropanoate (1.1 g, 81%): LC/MS (Table 2, Method f) Rt=1.95 min; MS m/z: 267 (M−H)−.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in DCM (100 mL)
  5. washThe organic solution was washed with saturated aqueous NaHCO3
  6. customthe layers were separated
  7. dry with materialThe organic solution was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customThe organic solution was directly purified by preparative TLC (1.0 mm plate)
  10. washeluting with 5:1 pet ether/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-5442342fc5eb4875bce3090f13f43747
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551981B2

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