Acetate → alpha-Hydroxyacetophenone

HRID 1650904Notes

Reaction equation

HRID 1650904 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[OH2:9].[N+]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-])=O>>[OH:9][CH2:2][C:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4]

Participants

5

Reactant 4

HCID 175AcetateHCID 962WaterHCID 7416NitrobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 68490alpha-HydroxyacetophenoneYield 64.9%

Procedure

To a solution of 755 mg of the thus-obtained acetate in nitrobenzene were added 456 mg of finely divided AlCl3, and the mixture was heated for one hour at 120°-125° C. The reaction mixture was diluted by water and extracted with ethyl acetate. The extracted solution was washed with water, sodium hydrogencarbonate solution, water, and saturated saline solution in series and dried over MgSO4. The distillation of the solvent and purification by chromatography through silica gel column gave 490 mg (yield: 64.9%) of the 2-hydroxyacetophenone.

Workup

  1. temperaturethe mixture was heated for one hour at 120°-125° C
  2. extractionextracted with ethyl acetate
  3. washThe extracted solution was washed with water, sodium hydrogencarbonate solution, water, and saturated saline solution in series
  4. dry with materialdried over MgSO4
  5. distillationThe distillation of the solvent and purification by chromatography through silica gel column

Sources & evidence

ORD record
ord-3f1b4eb596f64ace9a3303940ceb66c4
Source dataset
uspto-grants-1990_05
Patent number
US04925979

Reaction notes

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