Selenium Dioxide → 2-Methoxyphenylglyoxal hydrate

HRID 1154612Notes

Reaction equation

HRID 1154612 reaction equation
C[O:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[Se](=O)=O.[O:15]1CCOC[CH2:16]1>O.C(OCC)(=O)C>[OH2:2].[CH3:16][O:15][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]([CH:3]=[O:2])=[O:5]

Participants

6

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 776982-Methoxy-1-phenylethanone

Product 1

HCID 204341102-Methoxyphenylglyoxal hydrate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5 g of 2-methoxyacetophenone are dissolved in 30 ml of dioxane, and a solution of 4.8 g of selenium dioxide in 3 ml of water is added thereto. The mixture is refluxed for 6 hours. After the reaction is completed, insoluble materials are removed by filtration and the filtrate is condensed. The residue thus obtained is dissolved in ethyl acetate. The ethyl acetate solution is washed with water, an aqueous sodium bicarbonate solution and water, successively. Then, said solution is dried and evaporated to remove solvent. 4.9 g of 2-methoxyphenylglyoxal hydrate are thereby obtained as a crude oil.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. custominsoluble materials are removed by filtration
  3. customcondensed
  4. customThe residue thus obtained
  5. washThe ethyl acetate solution is washed with water
  6. customis dried
  7. customevaporated
  8. customto remove solvent

Sources & evidence

ORD record
ord-e72489dcc4e743c9bfc4a3ae879c2dd1
Source dataset
uspto-grants-1984_12
Patent number
US04490392

Reaction notes

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