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

HRID 973078Notes

Reaction equation

HRID 973078 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].O.[OH-].[Na+].[CH2:8](Br)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]>C(O)(=O)C.C(O)C>[C:1]([O:4][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6259Phenacyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 222851Ethanone, 2-(acetyloxy)-1-phenyl-

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent2×

Procedure

Five grams of acetic acid are added to 25 mls. of water in a suitable vessel and carefully neutralized with 10% aqueous sodium hydroxide. A few drops of acetic acid are then added until the solution is just acid to litmus paper. Fifty milliliters of ethanol and 5 grams of phenacyl bromide are then added and the mixture is refluxed for 1 hour. If a solid separates during refluxing additional ethanol is added to dissolve the same. The solution is allowed to cool and the phenacyl acetate is recovered by filtration and purified by recrystallization from ethanol, m.p. 47°-48° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. additionis added
  3. dissolutionto dissolve the same
  4. temperatureto cool
  5. filtrationthe phenacyl acetate is recovered by filtration
  6. custompurified by recrystallization from ethanol, m.p. 47°-48° C.

Sources & evidence

ORD record
ord-343f2d74b2884c858650f199d8ee7080
Source dataset
uspto-grants-1977_10
Patent number
US04054719

Reaction notes

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