Reaction #1249

Reaction equation

product

Ethyl 2,4-dioxo-4-(2,4,6-trimethylphenyl)butanoate

HCl

NaNO2

→

semi-solid

Ethyl 2,4-dioxo-3-oximino-4-(2,4,6-trimethylphenyl)butanoate

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe solvent was removed from the mixture and 200 mL of water
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   ExtractionThe product was then extracted into ether
4. 4
   ExtractionThe ether extract
5. 5
   Dryingwas dried over Na2SO4
6. 6
   Otherevaporated

Procedure

N2O3 gas was slowly passed into a stirred solution of the product of step A (16.2 g) in 300 mL of ethanol until the disappearance of starting material was confirmed by TLC. N2O3 gas was generated by the dropwise addition of 12N aqueous HCl solution into an aqueous slurry of NaNO2. The solvent was removed from the mixture and 200 mL of water was added to the residue. The product was then extracted into ether. The ether extract was dried over Na2SO4 and evaporated to give 16.1 g of a semi-solid.

Source