Acetic Acid → tert-butyl 2-hydroxyimino-3-oxobutanoate

HRID 1632720Notes

Reaction equation

HRID 1632720 reaction equation
[C:1]([O:5][C:6](=[O:11])[CH2:7][C:8]([CH3:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[N:16]([O-])=[O:17].[Na+]>O>[C:1]([O:5][C:6](=[O:11])[C:7](=[N:16][OH:17])[C:8]([CH3:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 15538Tert-butyl acetoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468384tert-butyl 2-hydroxyimino-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 158 g of acetoacetic acid-tert. butylester and 1000 ml of glacial acetic acid is added dropwise, while maintaining the temperature at 5°, a solution of 86.4 g of NaNO2 in 500 ml of water. After 4 hours stirring at 5°, the mixture is extracted 5 times with ether, the purified ether extracts are washed 5 times with water and twice with saturated sodium chloride and evaporated to dryness to obtain the heading compound, m.p. 55°-63°.

Workup

  1. additionis added dropwise
  2. temperaturewhile maintaining the temperature at 5°
  3. extractionthe mixture is extracted 5 times with ether
  4. washthe purified ether extracts are washed 5 times with water
  5. customtwice with saturated sodium chloride and evaporated to dryness
  6. customto obtain the heading compound, m.p. 55°-63°

Sources & evidence

ORD record
ord-1d3436bdde094838a7eac743fbce33b3
Source dataset
uspto-grants-1984_10
Patent number
US04477448

Reaction notes

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