Acetic Acid → HCID 13169281, compound

HRID 2285539Notes

Reaction equation

HRID 2285539 reaction equation
[CH:1]([O-])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Na+].[C:13](O)(=O)[CH3:14].O.[NH2:18][NH2:19].[C:20](=[O:23])([O-])[OH:21].[Na+]>O>[CH2:4]([C:3]1[NH:19][N:18]=[C:1]([C:20]([O:21][CH2:13][CH3:14])=[O:23])[CH:2]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)2×HCID 516892Sodium BicarbonateHCID 131712697HCID 131712697, compound

Product 1

HCID 13169281HCID 13169281, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 500 ml of absolute ethanol, 12.6 g (0.55 mol) of metallic sodium was added slowly to dissolve it completely under agitation, and after cooling, a mixed liquid of 78 g (0.55 mol) of methyl n-heptyl ketone and 80.3 g (0.55 mol) of diethyl oxalate was slowly dropped into the above-mentioned solution at room temperature under agitation. The stirring was continued for 8 hours after the addition, at room temperature. Then, the deposited yellow precipitate was collected by filtration and recrystallized from ethanol to obtain sodium 1-ethoxycarbonyl-3-oxo-1-decenolate as pale yellow needle-like crystals amounting to 117 g which corresponds to the yield of 80.0%. After dissolving 26.4 g (0.10 mol) of the thus prepared sodium decenolate into 23 ml of glacial acetic acid, 5.5 g (0.11 mol) of hydrazine hydrate was dropped slowly into the solution under ice cooling. After the addition of hydrazine hydrate, the mixture was heated under reflux for 8 hours. Then, the reaction mixture was cooled and poured into iced water, and then neutralized with an aqueous saturated solution of sodium hydrogen carbonate and extracted with benzene. The benzene layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. After distilling off the solvent under a reduced pressure, the residue was recrystallized from petroleum ether to obtain the object as colourless prisms amounting to 11.5 g which corresponds to the yield of 54.8% theoretical.

Workup

  1. additionwas dropped slowly into the solution under ice cooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 8 hours
  4. temperatureThen, the reaction mixture was cooled
  5. extractionextracted with benzene
  6. washThe benzene layer was washed with an aqueous saturated solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter distilling off the solvent under a reduced pressure
  9. customthe residue was recrystallized from petroleum ether
  10. customto obtain the object as colourless prisms amounting to 11.5 g which

Sources & evidence

ORD record
ord-247969a7763447c18bd927a177919fa0
Source dataset
uspto-grants-1982_04
Patent number
US04323576

Reaction notes

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