Phenacyl bromide → Ethanone, 2-(acetyloxy)-1-phenyl-

HRID 327756

Reaction equation

HRID 327756 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]([O:14]C(=O)C)(=[O:13])[CH3:12].C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:11]([O:14][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 7918Acetic AnhydrideHCID 517045Sodium Acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-bromoacetophenone (199 g, 1.0M), acetic acid (200 mL) and acetic anhydride (30 mL) was stirred and heated to about 60° C. Anhydrous sodium acetate (100 g, 1.2M) was added and the reaction mixture was heated and stirred at about 130° C. for 6.0 hrs and then allowed to cool. To remove most of the salt, the reaction mixture was filtered through a sintered glass funnel. The acetic acid and acetic anhydride were removed from the filtrate using a rotary evaporator. A white solid was obtained upon cooling (yield--97.0 g). Mass spectroscopy supported the proposed structure.

Workup

  1. temperaturethe reaction mixture was heated
  2. stirringstirred at about 130° C. for 6.0 hrs
  3. temperatureto cool
  4. customTo remove most of the salt
  5. filtrationthe reaction mixture was filtered through a sintered glass funnel
  6. customThe acetic acid and acetic anhydride were removed from the filtrate
  7. customa rotary evaporator
  8. customA white solid was obtained
  9. temperatureupon cooling
  10. custom(yield--97.0 g)

Sources & evidence

ORD record
ord-013b7c690e714cb1b9f2dbb4d4b29262
Source dataset
uspto-grants-1993_12
Patent number
US05274072

Linked notes

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