Methanol → Methyl 3-(2,4-dinitrophenyl)-2-methylpropanoate

HRID 1038851ノート

反応式

HRID 1038851 の反応式
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])([O-:3])=[O:2].OS(O)(=O)=O.[CH3:24]O>>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH:14]([CH3:18])[C:15]([O:17][CH3:24])=[O:16])([O-:3])=[O:2]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 662222213-(2,4-Dinitrophenyl)-2-methylpropanoic acid

生成物 1

HCID 86665113Methyl 3-(2,4-dinitrophenyl)-2-methylpropanoate収率 81%

実験手順

To a solution of 3-(2,4-dinitrophenyl)-2-methylpropanoic acid (1.6 g, 5.0 mmol) in MeOH (10 mL) was added H2SO4 (0.85 mL, 16 mmol) and the mixture was heated to reflux overnight. The solvent was removed under reduced pressure and the residue was dissolved in DCM (100 mL). The organic solution was washed with saturated aqueous NaHCO3 and the layers were separated. The organic solution was dried over anhydrous Na2SO4 and filtered. The organic solution was directly purified by preparative TLC (1.0 mm plate), eluting with 5:1 pet ether/EtOAc to give methyl 3-(2,4-dinitrophenyl)-2-methylpropanoate (1.1 g, 81%): LC/MS (Table 2, Method f) Rt=1.95 min; MS m/z: 267 (M−H)−.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in DCM (100 mL)
  5. washThe organic solution was washed with saturated aqueous NaHCO3
  6. customthe layers were separated
  7. dry with materialThe organic solution was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customThe organic solution was directly purified by preparative TLC (1.0 mm plate)
  10. washeluting with 5:1 pet ether/EtOAc

出典と根拠

ORDレコード
ord-5442342fc5eb4875bce3090f13f43747
出典データセット
uspto-grants-2013_10
特許番号
US08551981B2

反応ノート

読み込み中…