2,3-Dinitrophenol → 1-(2-Methoxy-ethoxy)-2,3-dinitro-benzene

HRID 18596

反応式

HRID 18596 の反応式
[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][O:23][CH3:24]>CC(C)=O>[CH3:24][O:23][CH2:22][CH2:21][O:13][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:4]=1[N+:1]([O-:3])=[O:2]

参加物

5

反応物 3

HCID 61912,3-DinitrophenolHCID 11430Potassium Carbonate2 回HCID 809722-Bromoethyl methyl ether2 回

生成物 1

HCID 865958811-(2-Methoxy-ethoxy)-2,3-dinitro-benzene

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

1.50 g (8.15 mmol) 2,3-Dinitro-phenol were dissolved in 75 mL acetone. Subsequently 1.69 g (12.22 mol) K2CO3, 135.3 mg KI (0.81 mmol) and 0.93 mL (9.77 mmol) 1-bromo-2-methoxy-ethane were added. The reaction mixture was refluxed for 8 h. After that time further 1.69 g (12.22 mol) K2CO3, 400 mg KI and 0.93 mL (9.77 mmol) 1-bromo-2-methoxy-ethane were added. The resulting mixture was refluxed for 16 h and then concentrated under reduced pressure. The residue was dissolved in warm ethyl acetate and purified by flash-chromatography on silica gel using an ethyl acetate/heptane-mixture as eluent to afford 1-(2-Methoxy-ethoxy)-2,3-dinitro-benzene as an orange crystalline material. Yield: 1.35 g MS (ES+): m/e=243.

後処理

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. temperatureThe resulting mixture was refluxed for 16 h
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in warm ethyl acetate
  5. custompurified by flash-chromatography on silica gel using an ethyl acetate/heptane-mixture as eluent

出典と根拠

ORDレコード
ord-f09b8a4915594338bcec72eb16b3d436
出典データセット
uspto-grants-2010_06
特許番号
US07741341B2

関連ノート

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