Ethanol → Diethyl isopropylmalonate

HRID 866692

Reaction equation

HRID 866692 reaction equation
C([C:3]([CH2:10][CH3:11])([C:7]([O-:9])=[O:8])[C:4]([O-:6])=[O:5])C.[O-][CH2:13][CH3:14].[Na+].Br[CH:17](C)[CH3:18].[CH2:20](O)C>>[CH:10]([CH:3]([C:7]([O:9][CH2:13][CH3:14])=[O:8])[C:4]([O:6][CH2:17][CH3:18])=[O:5])([CH3:11])[CH3:20]

Participants

5

Reactant 4

HCID 702EthanolHCID 63582-BromopropaneHCID 2723922Sodium ethoxideHCID 69515632,2-Diethylpropanedioate

Product 1

HCID 12966Diethyl isopropylmalonate

Procedure

Diethylmalonate (80.0g) in ethyl alcohol (50ml) was added to a solution of sodium ethoxide (prepared from sodium metal (13.0g) and absolute alcohol (400ml)) over 15 minutes whilst gently refluxing the mixture. After stirring under reflux for 1 hour a solution of 2-bromopropane (74.5g) in alcohol (50ml) was added over 1 hour and the mixture stirred under reflux overnight. The reaction mixture was cooled in ice and inorganic material removed by filtration and the filtrate concentrated. Water was added to the concentrate which was extracted with ether, the ethereal extracts washed with 2N sodium hydroxide solution (X2) and dried over magnesium sulphate. Removal of solvent gave an almost colourless liquid which was further purified by distillation to give diethyl isopropylmalonate b.p. 62°-65° C/0.7 mm Hg.

Workup

  1. temperaturegently refluxing the mixture
  2. additionwas added over 1 hour
  3. stirringthe mixture stirred
  4. temperatureunder reflux overnight
  5. temperatureThe reaction mixture was cooled in ice
  6. custominorganic material removed by filtration
  7. concentrationthe filtrate concentrated
  8. additionWater was added to the
  9. concentrationconcentrate which
  10. extractionwas extracted with ether
  11. washthe ethereal extracts washed with 2N sodium hydroxide solution (X2)
  12. dry with materialdried over magnesium sulphate
  13. customRemoval of solvent
  14. customgave an almost colourless liquid which
  15. distillationwas further purified by distillation

Sources & evidence

ORD record
ord-48a8a9dd81474627aa2b9c82b2f5bc23
Source dataset
uspto-grants-1978_07
Patent number
US04100363

Linked notes

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