Ethyl Acetoacetate → HCID 178472877, compound

HRID 1758543Notes

Reaction equation

HRID 1758543 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[N:10]([O-])=[O:11].[Na+]>C(O)(=O)C.O>[OH:11][N:10]=[C:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178472877HCID 178472877, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a cold (5°) stirred mixture of 3.9 kg. of ethyl acetoacetate in 2.25 liters of glacial acetic acid was added a solution of 2.25 kg. of sodium nitrite in 3 liters of water over one hour at 0°-15°. The reaction mixture was stirred at 0°-15° for six hours and worked up to give ethyl 2-hydroxyimino-acetoacetate (4.57 kg.) in 96% yield.

Workup

  1. additionmixture of 3.9 kg
  2. stirringThe reaction mixture was stirred at 0°-15° for six hours

Sources & evidence

ORD record
ord-b20edde27dab43ea82f6434c821fd874
Source dataset
uspto-grants-1983_02
Patent number
US04374252

Reaction notes

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