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

HRID 1443542Notes

Reaction equation

HRID 1443542 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].O>C(O)C>[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

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 107572-ChloroacetophenoneHCID 517044Potassium Acetate

Product 1

HCID 222851Ethanone, 2-(acetyloxy)-1-phenyl-Yield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 was heated under reflux in 500 ml of ethanol for 6 hours. After the completion of heating, the reaction solution was cooled to room temperature, precipitated potassium chloride was filtered off, and ethanol was evaporated off under reduced pressure, giving an oily and caramel-like substance. The obtained oily substance was poured into 1 liter of water and the precipitated yellowish-brown crystalline solid was filtered off, followed by recrystallization from methanol, giving 113.1 g (0.635 mol, 79.3% yield) 2-acetoxyacetophenone.

Workup

  1. temperatureAfter the completion of heating
  2. customprecipitated potassium chloride
  3. filtrationwas filtered off
  4. customethanol was evaporated off under reduced pressure
  5. customgiving an oily and caramel-like substance
  6. filtrationthe precipitated yellowish-brown crystalline solid was filtered off
  7. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-786a30af639e40e387f335d03bd3d6ad
Source dataset
uspto-grants-2010_02
Patent number
US07661577B2

Reaction notes

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