Acetic Acid → Phenylglyoxal

HRID 1685141Notes

Reaction equation

HRID 1685141 reaction equation
C(O)(=[O:3])C.O.[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[CH3:7]>O1CCOCC1>[O:8]=[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:7]=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 7410Acetophenone

Product 1

HCID 14090PhenylglyoxalYield 142%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Add SeO2 (4.6 g; 0.042 mol; 1.0 equiv), acetic acid (1.2 mL; 0.021 mol; 0.5 equiv), water (1.5 mL; 0.083 mol; 2.0 equiv) in 1,4-dioxane (15 mL) and stir at 80° C. until the solution becomes clear. Cool the reaction to RT, add acetophenone (5.0 g; 0.042 mol; 1.0 equiv) and stir at 80° C. for 18 h. Cool the reaction to RT, filter through Celite®, wash the residue with EA, and dry over anhydrous sodium sulfate. Evaporate the organic layer, purify over 50 g silica using EA in hexane to produce the title compound (4.0 g, 72.7%). MS (ES+): m/z=135 (M+H)

Workup

  1. temperatureCool
  2. customthe reaction to RT
  3. stirringstir at 80° C. for 18 h
  4. temperatureCool
  5. customthe reaction to RT
  6. filtrationfilter through Celite®
  7. washwash the residue with EA
  8. dry with materialdry over anhydrous sodium sulfate
  9. customEvaporate the organic layer
  10. custompurify over 50 g silica

Sources & evidence

ORD record
ord-1a4f93d7687d4ab0a57f0596d666ebff
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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