Nitromethane → 1,2,3-Trimethoxy-5-((E)-2-nitrovinyl)benzene

HRID 428126ノート

反応式

HRID 428126 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[N+:15]([CH3:18])([O-:17])=[O:16].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])/[CH:6]=[CH:18]/[N+:15]([O-:17])=[O:16]

参加物

5

反応物 3

HCID 6375NitromethaneHCID 68583,4,5-TrimethoxybenzaldehydeHCID 517165Ammonium Acetate

生成物 1

HCID 53549161,2,3-Trimethoxy-5-((E)-2-nitrovinyl)benzene収率 41%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 3,4,5-trimethoxybenzaldehyde (9.80 g, 50 mmol), nitromethane (18 ml), ammonium acetate (4.11 g) and acetic acid (38 ml) was heated and refluxed for 2 hours. After the reaction mixture was concentrated under reduced pressure, 10% aqueous sodium hydroxide solution was added to the residue and the reaction mixture was extracted with dichloromethane, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure and the residue was purified by silica gel chromatography (dichloromethane) and recrystallized to yield trans-3,4,5-trimethoxy-β-nitrostyrene (4.96 g, 41%). Properties: mp 116-118° C. (ethanol)

後処理

  1. temperaturewas heated
  2. temperaturerefluxed for 2 hours
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure, 10% aqueous sodium hydroxide solution
  4. additionwas added to the residue
  5. extractionthe reaction mixture was extracted with dichloromethane
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled out under reduced pressure
  9. customthe residue was purified by silica gel chromatography (dichloromethane)
  10. customrecrystallized

出典と根拠

ORDレコード
ord-10f4f322073948839ee1d7fbdcce32e8
出典データセット
uspto-grants-2001_11
特許番号
US06313153B1

反応ノート

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