4'-Hydroxypropiophenone → 4-Propanoylanisole

HRID 250515

Reaktionsgleichung

Reaktionsgleichung von HRID 250515
[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

Komponenten

5

Edukt 3

HCID 62714'-HydroxypropiophenoneHCID 6497Dimethyl SulfateHCID 11430Potassium Carbonate

Produkt 1

HCID 671444-Propanoylanisole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9c1f92022972431ea749753779867a42
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863313B2

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