Hydrochloric Acid → ethyl (2Z)-2-(3-benzoylphenyl)-2-hydroxyiminoacetate

HRID 584360Notes

Reaction equation

HRID 584360 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([C:15](=[N:18][OH:19])[C:16]#N)[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:20].[K+].[CH2:22]([OH:24])[CH3:23].Cl>C(OCC)(=O)C.CCCCCC>[C:1]([C:9]1[CH:10]=[C:11](/[C:15](=[N:18]/[OH:19])/[C:16]([O:24][CH2:22][CH3:23])=[O:20])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 738843482-(3-Benzoylphenyl)-2-(hydroxyimino)acetonitrile

Product 1

HCID 87950554ethyl (2Z)-2-(3-benzoylphenyl)-2-hydroxyiminoacetateYield 14%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 2-(3-benzoylphenyl)-2-(hydroxyimino)acetonitrile (14.5 g), 4N aqueous solution of potassium hydroxide (80 ml) and ethanol (80 ml) was heated under reflux for 20 hours. The reaction mixture was cooled to room temperature, 1N hydrochloric acid was added to make the solution acidic and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in ethanol (150 ml) and concentrated sulfuric acid (catalytic amount) was added. The reaction mixture was heated under reflux for 15 hours, cooled to room temperature, poured into an aqueous saturated solution of sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl Z-2-(3-benzoylphenyl)-2-(hydroxyimino)acetate (2.48 g, yield 14%) as a pale-brown oil from an ethyl acetate-hexane (1:2, v/v)-eluted fraction.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ethanol (150 ml)
  8. additionconcentrated sulfuric acid (catalytic amount) was added
  9. temperatureThe reaction mixture was heated
  10. temperatureunder reflux for 15 hours
  11. temperaturecooled to room temperature
  12. additionpoured into an aqueous saturated solution of sodium bicarbonate
  13. extractionextracted with ethyl acetate
  14. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  15. dry with materialdried (MgSO4)
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-120e30104ef641eeb1368c278ce30a17
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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