Diethyl Malonate → HCID 21491889, compound

HRID 1973506Notes

Reaction equation

HRID 1973506 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5]CC)=O.[C:12]1([CH3:23])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=[CH:19][C:20](=[O:22])[CH3:21]>[O-]CC.[Na+]>[O:5]=[C:3]1[CH2:21][C:20](=[O:22])[CH2:19][CH:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH3:23])[CH:2]1[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 140152HCID 140152, compound

Product 1

HCID 21491889HCID 21491889, compound

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

To a solution of sodium ethoxide (from 1.9 g.sodium and dry ethanol, 30 ml.) was added dropwise diethyl malonate (13 g.). After the addition the mixture was heated under reflux for 1 minute, cooled and then treated with 4-o-tolyl-3-buten-2-one. (13 g.). After heating under reflux for 17 hrs. the mixture was cooled and the precipitated sodium enolate salt (formula III) was collected by filtration, washed with acetone and then dissolved in cold water. The solution was acidified with 2N-H2SO4 and extracted with dichloromethane. After washing the organic solution with water and drying over Na2SO4, removal of solvents under reduced pressure afforded the corresponding dione II, i.e. ethyl 2,4-dioxo-6-o-tolylcyclohexanecarboxylate.

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 1 minute
  4. temperaturecooled
  5. temperatureAfter heating
  6. temperatureunder reflux for 17 hrs
  7. temperaturethe mixture was cooled
  8. filtrationthe precipitated sodium enolate salt (formula III) was collected by filtration
  9. washwashed with acetone
  10. dissolutiondissolved in cold water
  11. extractionextracted with dichloromethane
  12. washAfter washing the organic solution with water
  13. dry with materialdrying over Na2SO4, removal of solvents under reduced pressure

Sources & evidence

ORD record
ord-ff0d19a7822e465198c81fe8f38caa1d
Source dataset
uspto-grants-1976_12
Patent number
US03997590

Reaction notes

Loading…