Acetone → Diethylisopropylidene succinate

HRID 1708600Notes

Reaction equation

HRID 1708600 reaction equation
[H-].[Na+].[C:3]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:4][CH2:5][C:6]([O:8]CC)=[O:7].CC(C)=O.[C:19]1(C)[CH:24]=[CH:23]C=[CH:21][CH:20]=1>>[C:6]1(=[O:7])[O:8][C:13]([CH3:14])([CH:19]([CH2:24][CH3:23])[CH2:20][CH3:21])[O:12][C:3](=[O:11])[CH2:4][CH2:5]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 1140TolueneHCID 24758Sodium hydrideHCID 31249Diethyl Succinate

Product 1

HCID 54162692Diethylisopropylidene succinateYield 51%

Conditions

Temperature
40 °C

Procedure

Sodium hydride in an amount of 2 moles was suspended in 1.0 liter of toluene and heated at 40° C. To this, a mixed solution of 1 mole of diethyl succinate and 1.2 moles of acetone was added dropwise in 3 hours with stirring. The reaction was carried out for further 3 hours. Then, the reaction solution was poured into 1 kg of ice. The water layer was separated, made acidic by pouring 700 ml of 5M HCl thereinto, and extracted with 1.0 liter of 1,2-dichloroethane. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated. To the resulting residue, 1.0 liter of ethanol and 30 ml of concentrated sulfuric acid were added. The reaction was carried out under reflux for 4 hours. After the reaction, the solvent was removed from the reaction solution by distillation. The objected substance was extracted with dichloromethane and purified by distillation under reduced pressure to give diethylisopropylidene succinate in yield of 51%.

Workup

  1. customThe water layer was separated
  2. additionby pouring 700 ml of 5M HCl
  3. extractionextracted with 1.0 liter of 1,2-dichloroethane
  4. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionTo the resulting residue, 1.0 liter of ethanol and 30 ml of concentrated sulfuric acid were added
  7. temperatureunder reflux for 4 hours
  8. customAfter the reaction
  9. customthe solvent was removed from the reaction solution by distillation
  10. extractionThe objected substance was extracted with dichloromethane
  11. distillationpurified by distillation under reduced pressure

Sources & evidence

ORD record
ord-a19362817f8349c3a52a1dea1060b276
Source dataset
uspto-grants-1994_10
Patent number
US05359085

Reaction notes

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