4'-Hydroxyacetophenone → 29884-24-0

HRID 1779496Notes

Reaction equation

HRID 1779496 reaction equation
[O:1]=[C:2]([C:20]1[CH:34]=[CH:33][C:23]([O:24][C:25]([CH3:32])([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=1)[CH2:3]SC1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1.CC(C1C=CC(O)=CC=1)=O.BrC(C)(C)C(OCC)=O.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(C(C)=O)C(C)C>[C:2]([C:20]1[CH:34]=[CH:33][C:23]([O:24][C:25]([CH3:32])([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=1)(=[O:1])[CH3:3]

Participants

7

Reactant 4

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 19956261HCID 19956261, compound

Product 1

HCID 1234610829884-24-0

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

The ethyl 2-(4-acetylphenoxy)isobutyrate used as starting material was itself prepared as follows: 54.4 g of 4-hydroxyacetophenone, 375 ml of ethyl 2-bromoisobutyrate, 175 g of potassium carbonate, 1.2 liters of methyl isobutyl ketone and 3 g of potassium iodide are introduced into a three-necked flask equipped with a stirrer and a condenser. The whole is heated under reflux for 20 hours, then cooled, filtered and concentrated to dryness. The residue is chromatographed on 4 liters of Amicon silica (0.035-0.070 mm) while eluting with dichloromethane. The fractions retained are concentrated to dryness to yield 100 g of ethyl 2-(4-acetylphenoxy)isobutyrate in the form of a thick liquid (quantitative yield).

Workup

  1. customprepared
  2. customequipped with a stirrer and a condenser
  3. temperatureThe whole is heated
  4. temperatureunder reflux for 20 hours
  5. temperaturecooled
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue is chromatographed on 4 liters of Amicon silica (0.035-0.070 mm)
  9. washwhile eluting with dichloromethane
  10. concentrationThe fractions retained are concentrated to dryness

Sources & evidence

ORD record
ord-8774868f1fd04a6a8da22064c430c45b
Source dataset
uspto-grants-1997_05
Patent number
US05627205

Reaction notes

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