Chloroacetone → Diethyl (2-oxopropyl)propanedioate

HRID 1734140Notes

Reaction equation

HRID 1734140 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl[CH2:15][C:16](=[O:18])[CH3:17].C(OCC)(=O)C>CN(C)C=O>[O:18]=[C:16]([CH3:17])[CH2:15][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 7761Diethyl MalonateHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Product 1

HCID 12000252Diethyl (2-oxopropyl)propanedioateYield 43.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 25.0 g of diethyl malonate in 5 ml of dimethylformamide was added dropwise under ice-cooling over 20 minutes to a suspension of 6.55 g of sodium hydride in 90 ml of dimethylformamide. The reaction fluid was stirred for an hour under ice-cooling, to which a solution of 17.3 g of chloroacetone in 5 ml of dimethylformamide was added, and the mixture was stirred for an hour under ice-cooling and for 6 hours at room temperature. Ethyl acetate was added to the reaction fluid and the mixture was washed with water. The organic layer was dried over anhydrous magnesium sulfate. An oily matter obtained by concentrating the organic layer under a reduced pressure was distilled under vacuum to obtain 14.8 g of diethyl 2-oxopropylmalonate as a yellow oily matter.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for an hour under ice-
  3. washthe mixture was washed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customAn oily matter obtained
  6. concentrationby concentrating the organic layer under a reduced pressure
  7. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-05aa02cc3c784a47952a09379c435b2b
Source dataset
uspto-grants-1996_07
Patent number
US05532365

Reaction notes

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