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

HRID 428126노트

반응식

HRID 428126 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-10f4f322073948839ee1d7fbdcce32e8
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313153B1

반응 노트

불러오는 중…