Ethyl benzoylacetate → HCID 178472890, compound

HRID 880414Notes

Reaction equation

HRID 880414 reaction equation
[N:1]([O-:3])=O.[Na+].[CH3:5][CH2:6][O:7][C:8]([CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12])=[O:9]>O.C(O)(=O)C>[CH2:6]([O:7][C:8](=[O:9])[C:10](=[N:1][OH:3])[C:11](=[O:12])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:5]

Participants

5

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178472890HCID 178472890, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (56.5 g, 0.815 mol) in water (400 mL) was added to a solution of ethyl benzoyl acetate (120 g, 0.625 mol) in glacial acetic acid (300 mL) at 0-10° C. over a period of 2 h. The product started precipitating during the course of addition and the reaction mixture was warmed to room temperature and stirred for 30 min. Water (2.5 L) was added and the mixture was stirred for a further 30 min and then filtered under suction. The solid was washed with water (20 mL), petroleum ether (200 mL) and then dissolved in chloroform (700 mL). The filtrate was extracted with chloroform (2×100 mL) and the combined organic phase was washed with water (2×200 mL), brine solution (2×250 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford ethyl-2-hydroxyimino-3-oxo-3-phenyl-propanoate (122.5 g, 88%).

Workup

  1. customThe product started precipitating during the course of addition
  2. additionWater (2.5 L) was added
  3. stirringthe mixture was stirred for a further 30 min
  4. filtrationfiltered under suction
  5. washThe solid was washed with water (20 mL), petroleum ether (200 mL)
  6. dissolutiondissolved in chloroform (700 mL)
  7. extractionThe filtrate was extracted with chloroform (2×100 mL)
  8. washthe combined organic phase was washed with water (2×200 mL), brine solution (2×250 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5233227e27f4c4e96ff942b6fce4490
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

Loading…