4'-Hydroxypropiophenone → 4-Propanoylanisole

HRID 250515

反応式

HRID 250515 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[CH3:12][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 62714'-HydroxypropiophenoneHCID 6497Dimethyl SulfateHCID 11430Potassium Carbonate

生成物 1

HCID 671444-Propanoylanisole

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

To a solution of 4′-hydroxypropiophenone (1.0 g, 6.67 mmol) in acetonitrile (50.0 mL) was added potassium carbonate (7.17 g, 66.7 mmol) and the mixture heated to reflux for 90 min. After this time the reaction mixture was allowed to cool to room temperature and dimethyl sulphate (1.05 mL, 11.1 mmol) was added and the reaction mixture was heated to reflux for a further 19 h. After cooling the acetonitrile was evaporated under reduced pressure and the residue taken up in water and extracted with dichloromethane. The dichloromethane extract was dried (MgSO4) and evaporated under reduced pressure to give 4′-methoxypropiophenone as a yellow oil, (970 mg, 89%) 1H nmr (d6-DMSO, 300 MHz) 1.06, t (7.2 Hz), CH3; 2.95, q (7.2 Hz), CH2; 3.83, s, OMe; 7.02, d (6.9 Hz), H3′,5′; 7.93, d (6.9 Hz), H2′,6′. ESI (+ve) MS m/z 165 (M+H, 100%).

後処理

  1. temperaturethe mixture heated
  2. temperatureto reflux for 90 min
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for a further 19 h
  5. customwas evaporated under reduced pressure
  6. extractionextracted with dichloromethane
  7. extractionThe dichloromethane extract
  8. dry with materialwas dried (MgSO4)
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-9c1f92022972431ea749753779867a42
出典データセット
uspto-grants-2011_01
特許番号
US07863313B2

関連ノート

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