Acetic Acid → 2-Oxopropanal isopropylhydrazone

HRID 1880329Notes

Reaction equation

HRID 1880329 reaction equation
Cl.[CH:2]([NH:5][NH2:6])([CH3:4])[CH3:3].C(O)(=O)C.[CH:11](=O)[C:12]([CH3:14])=[O:13]>O>[CH:2]([NH:5][N:6]=[CH:11][C:12](=[O:13])[CH3:14])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 880MethylglyoxalHCID 855731-Isopropylhydrazine hydrochloride

Product 1

HCID 866504872-Oxopropanal isopropylhydrazoneYield 69.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of isopropylhydrazine hydrochloride (2.0 g, 18 mmol) in water (100 mL) was added acetic acid (1.7 mL) followed by the dropwise addition of pyruvaldehyde (2.6 g, 14.5 mmol) in water. The solution was stirred at room temperature overnight. The aqueous layer was extracted with CH2Cl2 (4×) and the combined organic extracts were washed with sat. aq. NaHCO3. The organic extract was dried over Na2SO4, filtered and concentrated to afford 2-oxopropanal isopropylhydrazone (1.3 g, 56%).

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2 (4×)
  2. washthe combined organic extracts were washed with sat. aq. NaHCO3
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-353c7a00660c45548282080a312558dd
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

Loading…