Acetic Acid → HCID 178472877, compound

HRID 1981636Notes

Reaction equation

HRID 1981636 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(O)(=O)C.[N:14]([O-])=[O:15].[Na+]>O>[N:14](=[C:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH2:8][CH3:9])=[O:6])[OH:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178472877HCID 178472877, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suitable reaction vessel was charged with 0.385 mol of ethyl acetoacetate and 0.87 mol of acetic acid and cooled in an ice bath. A solution of 0.435 mol of sodium nitrite in 50 ml of water was added dropwise to the reaction mixture over a period of about 30 minutes, and the resultant reaction mixture was stirred until its color went from clear to light orange. The ice bath was then removed and stirring continued for an additional two hours, another 140 ml of water being added 30 minutes into this two-hour stirring period. Work-up of the reaction mixture resulted in the isolation of ethyl 2-oximinoacetoacetate in a 95% yield.

Workup

  1. temperaturecooled in an ice bath
  2. customthe resultant reaction mixture
  3. customThe ice bath was then removed
  4. stirringstirring
  5. additionanother 140 ml of water being added 30 minutes into this two-hour
  6. stirringstirring period

Sources & evidence

ORD record
ord-2a31d4a8d0524a8fa2e86d4d8a0fbd1c
Source dataset
uspto-grants-1986_06
Patent number
US04593118

Reaction notes

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