Nitromethane → Methyl 4-(2-nitroethenyl)benzoate

HRID 415328

反応式

HRID 415328 の反応式
[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]

参加物

4

反応物 3

HCID 6375NitromethaneHCID 15294Methyl 4-FormylbenzoateHCID 517165Ammonium Acetate

生成物 1

HCID 896295Methyl 4-(2-nitroethenyl)benzoate収率 62%

反応条件

温度
120 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-f823019cc906481b9b2f140e13b4a711
出典データセット
uspto-grants-2012_01
特許番号
US08088760B2

関連ノート

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