Oxygen → Acetophenone

HRID 1641598Notes

Reaction equation

HRID 1641598 reaction equation
[OH:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10].O=O>C(O)(=O)C.O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:1])[CH3:10]

Participants

6

Reactant 3

HCID 977OxygenHCID 7500EthylbenzeneHCID 80170N-Hydroxysuccinimide

Product 1

HCID 7410AcetophenoneYield 80%

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
30 °C

Procedure

In this example, a solution of 0.1158 g (1.01 mmol) of N-hydroxysuccinimide, 0.544 g (5.13 mmol) of ethylbenzene and 0.1158 g (0.46 mmol) of cobalt acetate tetrahydrate in 40 ml of acetic acid was heated to 30° C. in a Parr Hastelloy reactor with temperature and pressure transducer. After the temperature reached 30° C., 233 psi of air was slowly introduced to the reactor. The mixture was stirred under pressure for one hour at 30° C., then the pressure was released, and the mixture was cooled to room temperature. A slow temperature rise (due to heat generated by the exothermic oxidation) within roughly 30 minutes following O2 introduction, accompanied by a drop in reactor pressure (due to consumption of O2 in the liquid phase reaction) indicates rapid reaction following induction. These profiles are steep and level off within minutes after induction. The reaction product mixture was extracted by ethyl acetate, then washed by water and saturated NaCl, dried over Na2SO4 to give acetophenone 80% and starting material 20% analysis by GC-MS and HPLC.

Workup

  1. customreached 30° C.
  2. addition233 psi of air was slowly introduced to the reactor
  3. temperaturethe mixture was cooled to room temperature
  4. temperatureA slow temperature rise (due to heat
  5. customwithin roughly 30 minutes
  6. customaccompanied by a drop in reactor
  7. custompressure (due to consumption of O2
  8. customin the liquid phase reaction)
  9. customreaction
  10. extractionThe reaction product mixture was extracted by ethyl acetate
  11. washwashed by water and saturated NaCl
  12. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-fb9164b6b7084fb2847dcdf8d993f07f
Source dataset
uspto-grants-2012_02
Patent number
US08115029B2

Reaction notes

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