Ethanol → Ethyl 4-hydroxy-3-methoxy-5-nitrophenylglyoxylate

HRID 1781812Notes

Reaction equation

HRID 1781812 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([O:15][CH3:16])[CH:6]=1)=[O:4].[Se](=O)=[O:18].[CH2:20]([OH:22])[CH3:21]>>[OH:14][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([C:3](=[O:4])[C:2]([O:22][CH2:20][CH3:21])=[O:18])=[CH:6][C:7]=1[O:15][CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 24007Selenium DioxideHCID 144509832-Bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone

Product 1

HCID 14450984Ethyl 4-hydroxy-3-methoxy-5-nitrophenylglyoxylate

Procedure

ba) A suspension of 580.1 mg of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone in 10 ml of ethanol is treated with 443.8 mg of selenium dioxide and heated under reflux for 71 hours. Thereafter, the selenium is removed by filtration and the filtrate is evaporated. The residue is dissolved in methylene chloride, washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. There is obtained ethyl 4-hydroxy-3-methoxy-5-nitrophenylglyoxylate of m.p. 165°-167° (from ethanol).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 71 hours
  3. customThereafter, the selenium is removed by filtration
  4. customthe filtrate is evaporated
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-657381fee6594bcc800e24778971091f
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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