Acetic Acid → HCID 178472906, compound

HRID 256420Notes

Reaction equation

HRID 256420 reaction equation
[C:1]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:4])[CH2:2][CH3:3].C(O)(=O)C.[N:15]([O-])=[O:16].[Na+]>O>[C:1]([C:5](=[N:15][OH:16])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:4])[CH2:2][CH3:3]

Participants

5

Procedure

Ethyl propionylacetate (14.4 g.) was added to acetic acid (19 ml.) and stirred at 5° to 10° C. To the solution was added dropwise over 40 minutes about 2/3 volume of an aqueous solution (30 ml.) of sodium nitrite (15 g.), and further water (50 ml.) was added to the solution and stirred at 25° C. for 1.5 hrs. The remaining aqueous solution of sodium nitrite was added dropwise over 10 minutes to the solution and stirred at room temperature for 2 hrs. The reaction mixture was extracted with diethyl ether (50 ml.) twice, and the extract was washed with saturated aqueous sodium bicarbonate (30 ml.) three times and saturated aqueous sodium chloride, dried over magnesium sulfate and filtered. The filtrate was evaporated in vacuo to give ethyl 2-propionyl-2-hydroxyiminoacetate (12 g.).

Workup

  1. additionwas added to the solution
  2. stirringstirred at 25° C. for 1.5 hrs
  3. stirringstirred at room temperature for 2 hrs
  4. extractionThe reaction mixture was extracted with diethyl ether (50 ml.) twice
  5. washthe extract was washed with saturated aqueous sodium bicarbonate (30 ml.) three times and saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-b8cd8298063b4536b4c365490ce810d7
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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