Nitromethane → Methyl 4-(2-nitroethenyl)benzoate

HRID 415328

Reaktionsgleichung

Reaktionsgleichung von HRID 415328
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.C([O-])(=O)C.[NH4+].[N+:18]([CH3:21])([O-:20])=[O:19]>>[N+:18]([CH:21]=[CH:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)([O-:20])=[O:19]

Komponenten

4

Edukt 3

HCID 6375NitromethaneHCID 15294Methyl 4-FormylbenzoateHCID 517165Ammonium Acetate

Produkt 1

HCID 896295Methyl 4-(2-nitroethenyl)benzoateAusbeute 62 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of methyl 4-formylbenzoate (34 g, 207 mmol) in nitromethane (500 mL) was added ammonium acetate (24 g, 311 mmol) and then the mixture was stirred at 120° C. for 1 h. Evaporated the solvent and diluted with ethyl acetate, the mixture was hydrolyzed and extracted. The organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to obtain methyl 4-(2-nitrovinyl)benzoate as a yellow solid (26.6 g, yield 62%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.87 (s, 3H), 7.09-8.04 (m, 4H), 8.17-8.21 (d, J=14 Hz, 1H), 8.30-8.34 (d, J=14 Hz, 1H). LC-MS (ESI) m/z: 208 (M+1)+.

Aufarbeitung

  1. customEvaporated the solvent
  2. additiondiluted with ethyl acetate
  3. extractionextracted
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f823019cc906481b9b2f140e13b4a711
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088760B2

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