Ethanol → alpha-Hydroxyacetophenone

HRID 2185141Notes

Reaction equation

HRID 2185141 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].BrCC(C1C=CC=CC=1)=[O:14].O.CCO>CN(C=O)C>[OH:14][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 6259Phenacyl bromideHCID 107572-Chloroacetophenone

Product 1

HCID 68490alpha-HydroxyacetophenoneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloroacetophenone derivatives (or 2-bromoacetophenone derivatives, 0.19 mol), NaOOCH (0.59 mol) in DMF (140 mL), H2O (100 mL) and EtOH (400 mL) was heated under refluxing. After 5-8 hrs, the reaction mixture was cooled to room temperature, then about half of the solvent was removed under vacuum. The residue was diluted with water, and extracted with CH2Cl2. The combined organic layer was washed by H2O, followed by brine;. After drying over Na2SO4, solvents were evaporated under vacuum. The crude product was washed with hexanes, filtration gave the desired 2-hydroxyacetophenone derivatives as a solid in 70˜85% yield, which were used directly for the next step.

Workup

  1. temperatureunder refluxing
  2. customabout half of the solvent was removed under vacuum
  3. additionThe residue was diluted with water
  4. extractionextracted with CH2Cl2
  5. washThe combined organic layer was washed by H2O
  6. dry with materialAfter drying over Na2SO4, solvents
  7. customwere evaporated under vacuum
  8. washThe crude product was washed with hexanes, filtration

Sources & evidence

ORD record
ord-a8f3104628b04935940be307bb7272e7
Source dataset
uspto-grants-2002_06
Patent number
US06399787B1

Reaction notes

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