Hydrogen Peroxide → HCID 12272043, compound

HRID 893245Notes

Reaction equation

HRID 893245 reaction equation
[CH:1](=[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[OH:14]O>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+].C(O)C>[CH3:2][CH:1]1[O:14][C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 73831Propanedioic acid, ethylidene-, diethyl ester

Product 1

HCID 12272043HCID 12272043, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 150191Sodium Tungstate DihydrateCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 50 grams (0.27 mole) of diethyl ethylidenemalonate, 455 grams (4.02 moles) of 30% hydrogen peroxide, 17.6 gram (0.053 mole) of sodium tungstate dihydrate and 400 milliliters of ethanol was stirred and heated at 80° C. for one hour, cooled to room temperature and stirred for an additional hour. Ethanol was removed under reduced pressure and the produce extracted into dichloromethane (3×200 milliliters), the extract then water-washed, dried (MgSO4), filtered and solvent removed to give the crude product. Vacuum distillation gave 40.45 grams (0.20 mole) of diethyl 3-methyloxirane-2,2-dicarboxylate having a boiling point of 120° C. at 4millimeters of Hg.

Workup

  1. temperaturecooled to room temperature
  2. stirringstirred for an additional hour
  3. customEthanol was removed under reduced pressure
  4. extractionthe produce extracted into dichloromethane (3×200 milliliters)
  5. extractionthe extract
  6. washwater-washed
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customsolvent removed
  10. customto give the crude product
  11. distillationVacuum distillation

Sources & evidence

ORD record
ord-5aae2dcc90ed4551ac6e2e60ebc6022c
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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