4'-Fluoroacetophenone → (4-Fluorophenyl)glyoxal

HRID 2407069Notes

Reaction equation

HRID 2407069 reaction equation
[Se](=O)=[O:2].[CH3:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6]>O1CCOCC1.O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]([CH:4]=[O:2])=[O:6])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 98284'-FluoroacetophenoneHCID 24007Selenium Dioxide2×

Product 1

HCID 101249(4-Fluorophenyl)glyoxalYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Selenium dioxide (6.70 g, 61.0 mmol) was added to a solution of 4-fluoroacetophenone (8.43 g, 61.0 mmol) in dioxane (100 mL) and water (3 mL), and the resulting mixture was heated at 55° C. until complete dissolution of selenium dioxide had occurred. The reaction mass was then refluxed for 5-6 hrs. After completion of the reaction (TLC), the mixture was filtered and the filtrate was concentrated in vacuo affording a viscous oil. Water (50 mL) was added and the resulting mixture was stirred for 12 hrs, after which time the solid was collected on a filter, washed with water (25 mL) and dried in vacuo, affording 4-fluorophenylglyoxal (6.60 g, 85%).

Workup

  1. temperatureThe reaction mass was then refluxed for 5-6 hrs
  2. customAfter completion of the reaction (TLC)
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customaffording a viscous oil
  6. customafter which time the solid was collected on a filter
  7. washwashed with water (25 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-487918979a474c1ebf6462d2211f82f3
Source dataset
uspto-grants-2014_08
Patent number
US08809525B2

Reaction notes

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