Hydrochloric Acid → 4-Amino-2,5-dimethylbenzaldehyde

HRID 1627983

反応式

HRID 1627983 の反応式
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].Cl.[OH-:11].[Na+].[CH3:13]S(C)=O>[Cu](Cl)Cl>[NH2:4][C:3]1[C:2]([CH3:1])=[CH:8][C:7]([CH:13]=[O:11])=[C:6]([CH3:9])[CH:5]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 72592,5-DimethylanilineHCID 14798Sodium Hydroxide

生成物 1

HCID 552846924-Amino-2,5-dimethylbenzaldehyde収率 22.8%

試薬・触媒・溶媒 1

HCID 24014Cupric Chloride触媒

反応条件

温度
90 °C

実験手順

6.06 g (50.0 mmol) of 2,5-dimethylaniline are initially charged in 1000 ml of DMSO, 13.55 g (100.0 mmol) of copper(II) chloride are added and concentrated hydrochloric acid is then added slowly. The reaction mixture is heated at 90° C. for 3 h and then added to ice-water. After addition of aqueous sodium hydroxide solution, the mixture is filtered and extracted repeatedly with ethyl acetate, and the combined organic phases are dried over Na2SO4 and freed from solvent under reduced pressure. The crude product is purified by column chromatography. (2.27 g, purity 75.0%, yield 22.8%, log P (pH 2.3)=1.34).

後処理

  1. filtrationthe mixture is filtered
  2. extractionextracted repeatedly with ethyl acetate
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. customThe crude product is purified by column chromatography

出典と根拠

ORDレコード
ord-ec3bafc94f814d3ebc3cd16ce5a90227
出典データセット
uspto-grants-2014_07
特許番号
US08785692B2

関連ノート

読み込み中…