Selenium Dioxide → 2-Ethoxyphenylglyoxal

HRID 66324Notes

Reaction equation

HRID 66324 reaction equation
C([O:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])C.[Se](=O)=O.[O:16]1CCO[CH2:18][CH2:17]1>O.C(OCC)(=O)C>[CH2:17]([O:16][C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:5]([CH:4]=[O:3])=[O:6])[CH3:18]

Participants

6

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 1398412-Ethoxy-1-phenylethan-1-one

Product 1

HCID 227549162-Ethoxyphenylglyoxal

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2 g of 2-ethoxyacetophenone are dissolved in 20 ml of dioxane, and a solution of 2 g of selenium dioxide in one ml of water is added thereto. The solution is refluxed for 10 hours. After the reaction, insoluble materials are removed by filtration, and the filtrate is concentrated. The residue thus obtained is dissolved in ethyl acetate. The ethyl acetate solution is washed with water and then with an aqueous sodium bicarbonate solution and water. Then, said solution is dried and evaporated to remove solvent. 2.1 g of 2-ethoxyphenylglyoxal are obtained as a crude oil.

Workup

  1. temperatureThe solution is refluxed for 10 hours
  2. customAfter the reaction, insoluble materials
  3. customare removed by filtration
  4. concentrationthe filtrate is concentrated
  5. customThe residue thus obtained
  6. washThe ethyl acetate solution is washed with water
  7. customis dried
  8. customevaporated
  9. customto remove solvent

Sources & evidence

ORD record
ord-74c949b65bbb45b78134c4849088b0f2
Source dataset
uspto-grants-1978_12
Patent number
US04131686

Reaction notes

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