Acetic Acid → 4'-Hydroxypropiophenone

HRID 1925580Notes

Reaction equation

HRID 1925580 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.C(O)(=O)C>Br(O)(=O)=O.C(OCC)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 671444-Propanoylanisole

Product 1

HCID 62714'-HydroxypropiophenoneYield 69,891.102%

Reagents, catalysts & solvents 2

HCID 24445Bromic acidCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

While 20 g (0.121 mmol) of 1-(4-methoxyphenyl)-1-propanone (7) prepared in Example 1-2 were added to 139 ml (2.4 mol) of acetic acid and stirred, 270 ml (2.4 mmol) of 48% bromic acid were added. Subsequently, the temperature was gradually increased to 100° C. and stirring under reflux was continued for 18 hr. The temperature was decreased to room temperature, and ethyl acetate was added, and organic layer was washed with water. Thereafter, the organic layer was washed with a saturated aqueous solution of potassium carbonate, then concentrated under reduced pressure, after which the precipitated solid was recrystallized with ethyl acetate/n-hexane system, and filtered, thus obtaining 12.7 g (yield: 70%) of a title compound (8) as a solid.

Workup

  1. stirringstirring
  2. temperatureunder reflux
  3. customwas decreased to room temperature
  4. washorganic layer was washed with water
  5. washThereafter, the organic layer was washed with a saturated aqueous solution of potassium carbonate
  6. concentrationconcentrated under reduced pressure
  7. customafter which the precipitated solid was recrystallized with ethyl acetate/n-hexane system
  8. filtrationfiltered

Sources & evidence

ORD record
ord-90f423b72ad5408eadcdc7874d9aa93c
Source dataset
uspto-grants-2012_05
Patent number
US08178688B2

Reaction notes

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