Nitromethane → Benzenepropanoic acid, b-(nitromethyl)-, methyl ester

HRID 1045677

Reaktionsgleichung

Reaktionsgleichung von HRID 1045677
[C:1]([O:11][CH3:12])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:13]([CH3:16])([O-:15])=[O:14]>>[CH3:12][O:11][C:1](=[O:10])[CH2:2][CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:16][N+:13]([O-:15])=[O:14]

Komponenten

3

Edukt 2

HCID 6375NitromethaneHCID 76442-Propenoic acid, 3-phenyl-, methyl ester

Produkt 1

HCID 10537045Benzenepropanoic acid, b-(nitromethyl)-, methyl esterAusbeute 59 %

Versuchsvorschrift

A solution of methyl cinnamate (4.93 g, 30.4 mmol) and teteramethylguanidine (3.99 g, 34.6 mmol) in nitromethane (30 ml) was stirred for 6 hours at 90° C. After removal of the solvent under reduced pressure, the residue was partitioned between water and ethyl acetate, and the organic layer was washed with water and brine and then dried over sodium sulfate. The organic solvents were removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=4/1) to afford 4-nitro-3-phenyl-butyric acid methyl ester (4.02 g, 59%)

Aufarbeitung

  1. customAfter removal of the solvent under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe organic solvents were removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-c8e60e5b5cfc4570bdec6bafcfa9603c
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569294B2

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