Selenium Dioxide → 2-Methoxyphenylglyoxal hydrate

HRID 1680877Notes

Reaction equation

HRID 1680877 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>[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

5

Reactant 3

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

Product 1

HCID 204341102-Methoxyphenylglyoxal hydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 750 mg of 2-methoxyacetophenone, 722 mg of selenium dioxide, 8 ml of 1,4-dioxane and 0.3 ml of water is refluxed for 6 hours. After cooling, the precipitates are collected by filtration, and then washed with benzene. The filtrate and the washing are combined, and the combined solution is evaporated to remove solvent. The residue (orange yellow oil) is dissolved in benzene, and the solution is washed with a saturated sodium chloride solution, a saturated sodium bicarbonate solution and a saturated sodium chloride solution, successively. The washed solution is dried and then evaporated to remove solvent. 554 mg of 2-methoxyphenylglyoxal hydrate are thereby obtained as a yellow oil.

Workup

  1. temperatureis refluxed for 6 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitates are collected by filtration
  4. washwashed with benzene
  5. customthe combined solution is evaporated
  6. customto remove solvent
  7. dissolutionThe residue (orange yellow oil) is dissolved in benzene
  8. washthe solution is washed with a saturated sodium chloride solution
  9. customThe washed solution is dried
  10. customevaporated
  11. customto remove solvent

Sources & evidence

ORD record
ord-08189c0261214b7598d0e3ebe6cb5bfb
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

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