Nitromethane → Methyl 4-(2-nitroethenyl)benzoate

HRID 415328

Reaction equation

HRID 415328 reaction equation
[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]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 15294Methyl 4-FormylbenzoateHCID 517165Ammonium Acetate

Product 1

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

Conditions

Temperature
120 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-f823019cc906481b9b2f140e13b4a711
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Linked notes

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