2,3-Dimethylanisole → 2-Methoxy-6-methylbenzaldehyde

HRID 2036042ノート

反応式

HRID 2036042 の反応式
S1(OS(=O)(=O)OOOO1)(=O)=O.[K].[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[O:21][CH3:22].C(OCC)(=[O:25])C.CCCCCC>O.C(#N)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:22][O:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[C:14]=1[CH:13]=[O:25]

参加物

6

反応物 3

HCID 762692,3-DimethylanisoleHCID 21226206Ethyl acetate hexaneHCID 86652980Potassium peroxy disulphate

生成物 1

HCID 6402382-Methoxy-6-methylbenzaldehyde収率 44.2%

試薬・触媒・溶媒 2

HCID 24463Copper sulfate pentahydrate触媒HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

Potassium peroxy disulphate (89.31 g, 0.33 mol) and copper (II) sulphate pentahydrate (27.22 g, 0.11 mol) was added to a solution of 2,3-dimethylanisole (15 g, 0.11 mol) in acetonitrile water mixture (750 ml, 1:1). The reaction mixture was stirred for 15 min at reflux until no starting material remained as judged by TLC (Thin Layer Chromatography). On cooling the reaction mixture to room temperature, the product was extracted into dichloromethane (2×225 ml). The organic layer was washed with water (2×100 ml) and brine solution (100 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product. Column chromatography using 4/96 ethyl acetate/hexane yielded 2-Methoxy-6-methylbenzaldehyde (7.32 g, 44.2%).

後処理

  1. temperatureat reflux until no starting material
  2. extractionthe product was extracted into dichloromethane (2×225 ml)
  3. washThe organic layer was washed with water (2×100 ml) and brine solution (100 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product

出典と根拠

ORDレコード
ord-2d879bee0a704ed7b2f08809380094d4
出典データセット
uspto-grants-2013_11
特許番号
US08575161B2

反応ノート

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