4'-Hydroxypropiophenone → 4-Propanoylanisole

HRID 250515Notes

Reaction equation

HRID 250515 reaction equation
[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

Participants

5

Reactant 3

HCID 62714'-HydroxypropiophenoneHCID 6497Dimethyl SulfateHCID 11430Potassium Carbonate

Product 1

HCID 671444-Propanoylanisole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-9c1f92022972431ea749753779867a42
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

Loading…