Acetic Acid → Ethanone, 2-(acetyloxy)-1-phenyl-

HRID 389225

Reaction equation

HRID 389225 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].C(O)(=O)C.Cl[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].[Cl-].[K+]>C(O)C.O>[C:1]([O:4][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4873Potassium ChlorideHCID 107572-ChloroacetophenoneHCID 517044Potassium Acetate

Product 1

HCID 222851Ethanone, 2-(acetyloxy)-1-phenyl-Yield 79.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

78.5 g (0.80 mol) of potassium acetate, 5.0 g (0.08 mol) of acetic acid, and 123.7 g (0.80 mol) of 2-chloroacetophenone were heated under reflux in 500 mL of ethanol for 6 hours. After completion of heating, the reaction mixture was cooled to room temperature, deposited potassium chloride was filtered off, and the ethanol was distilled off in vacuo to obtain a pale brown oily material. This oily material was poured into one litter of water, and a precipitated solid was collected by filtration and recrystallized from methanol to obtain 113.1 g (yield: 79.3%) of 2-acetoxyacetophenone as a pale yellow solid.

Workup

  1. temperatureAfter completion of heating
  2. filtrationwas filtered off
  3. distillationthe ethanol was distilled off in vacuo
  4. customto obtain a pale brown oily material
  5. filtrationa precipitated solid was collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-fc2654983c52434986fb0f4c03a16532
Source dataset
uspto-grants-2013_02
Patent number
US08378116B2

Linked notes

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