Selenium Dioxide → 2-(3-(Benzyloxy)phenyl)-2-oxoacetaldehyde

HRID 261603Notes

Reaction equation

HRID 261603 reaction equation
[Se](=O)=O.[O:4]1CCOCC1.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]=1)=[O:12]>O>[CH2:20]([O:19][C:15]1[CH:14]=[C:13]([C:11]([CH:10]=[O:4])=[O:12])[CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-one

Product 1

HCID 134580312-(3-(Benzyloxy)phenyl)-2-oxoacetaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 9.4 g. of selenium dioxide in a solvent mixture of 50 ml. of dioxane and 1.7 ml. of water, was added 16.5 g. of 3-benzyloxyacetophenone. The mixture was refluxed for 4 hrs. with stirring. The resulting precipitates were removed by filtration and the solvents were distilled off from the filtrate under reduced pressure. The residue was dissolved in benzene and washed with water several times. After drying the benzene layer, benzene was removed by distillation to obtain the glyoxal as yellow liquid in a quantitative yield.

Workup

  1. temperatureThe mixture was refluxed for 4 hrs
  2. customThe resulting precipitates
  3. customwere removed by filtration
  4. distillationthe solvents were distilled off from the filtrate under reduced pressure
  5. dissolutionThe residue was dissolved in benzene
  6. washwashed with water several times
  7. dry with materialAfter drying the benzene layer, benzene
  8. customwas removed by distillation

Sources & evidence

ORD record
ord-5c05fd5f8379424e8e6798a5a0ae7acd
Source dataset
uspto-grants-1979_08
Patent number
US04166180

Reaction notes

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