Acetic Acid → 2-Oxopropanal propylhydrazone

HRID 1880336Notes

Reaction equation

HRID 1880336 reaction equation
C(O)(=O)C.C(O)(=O)C(O)=O.[CH2:11]([NH:14][NH2:15])[CH2:12][CH3:13].[CH:16](=O)[C:17]([CH3:19])=[O:18]>O>[CH2:11]([NH:14][N:15]=[CH:16][C:17](=[O:18])[CH3:19])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 880MethylglyoxalHCID 96079Hydrazine, propyl-, ethanedioate (1:1)

Product 1

HCID 866504882-Oxopropanal propylhydrazoneYield 119.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Acetic acid (2.9 mL, 50 mmol) was added to a solution of n-propylhydrazine oxalate (5.0 g, 30 mmol) in water (100 mL). This mixture was added to a solution of pyruvaldehyde (4.39 g, 3.96 mL, 24.4 mmol) in water (500 mL). The solution was stirred at room temperature overnight. The aqueous phase was extracted with CH2Cl2 (4×) and the combined organic extracts were washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated to afford 2-oxopropanal propylhydrazone (3.74 g, 96%).

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2 (4×)
  2. washthe combined organic extracts were washed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7796eb213dd844c38e6977f5798fc803
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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