Water → Allylmalonic acid

HRID 52681Notes

Reaction equation

HRID 52681 reaction equation
[OH-].[K+].O.C([O:7][C:8](=[O:17])[C:9]([CH2:15][CH3:16])(CC)[C:10]([O-:12])=[O:11])C=C.[CH3:18]CCCCCC>>[CH2:15]([CH:9]([C:8]([OH:7])=[O:17])[C:10]([OH:12])=[O:11])[CH:16]=[CH2:18]

Participants

5

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 14797Potassium HydroxideHCID 86749454Allyldiethylmalonate

Product 1

HCID 75748Allylmalonic acid

Procedure

Potassium hydroxide (15.6 g, 0.28 mol), 15 ml of distilled water and 50 ml of heptane are added to a round bottom flask. Allyldiethylmalonate (22.0 g, 1.1 mol) is added slowly to the reaction mixture with stirring and refluxed for sufficient time to complete hydrolysis. Ethanol is removed with a rotoevaporator. The resultant product is cooled in a beaker and acidified with sulfuric acid. The final solution is extracted with diethylether. The ether layer is collected, dried over MgSO4, and ether is removed with a rotoevaporator. The crude allylmalonic acid is crystalized from petroleum ether.

Workup

  1. temperaturerefluxed for sufficient time
  2. customhydrolysis
  3. customEthanol is removed with a rotoevaporator
  4. temperatureThe resultant product is cooled in a beaker
  5. extractionThe final solution is extracted with diethylether
  6. customThe ether layer is collected
  7. dry with materialdried over MgSO4, and ether
  8. customis removed with a rotoevaporator
  9. customThe crude allylmalonic acid is crystalized from petroleum ether

Sources & evidence

ORD record
ord-349213c5f9ac4571b5aa951a51b8ff05
Source dataset
uspto-grants-1997_04
Patent number
US05616757

Reaction notes

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