Diethyl methylmalonate → HCID 19909285, compound

HRID 1649620Notes

Reaction equation

HRID 1649620 reaction equation
[Na].C[CH:3]([C:9]([O:11]CC)=O)[C:4]([O:6]CC)=O.[C:14]([C:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1)(=O)[CH3:15].[OH-].[K+]>C(O)C.O>[CH3:15][CH:14]1[CH:17]2[CH:18]([CH2:19][CH2:20][CH2:21][CH2:22]2)[C:4](=[O:6])[CH2:3][C:9]1=[O:11]

Participants

7

Reactant 4

HCID 11857Diethyl methylmalonateHCID 136121-AcetylcyclohexeneHCID 14797Potassium HydroxideHCID 5360545Sodium

Product 1

HCID 19909285HCID 19909285, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium metal (2.31 g, 101.0 mmol) is dissolved in 50 ml of ethanol, and diethyl methylmalonate (17.6 g, 101.0 mmol) is added, after which the mixture is stirred for approx. 30 min. under reflux. 1-Acetyl-1-cyclohexene (12.50 g, 101.0 mmol) is added and the mixture is stirred under reflux overnight. Potassium hydroxide (12.47 g, 222.2 mmol) dissolved in 40 ml of water is added and the mixture is heated under reflux for 4 hr. The ethanol is removed by rotary evaporation, and the residue is dissolved in water and washed with ether. The aqueous layer is acidified with conc. HCl and extracted with ether. The combined extracts are dried and the solvent is removed to give 4a,5,6,7,8,8a -hexahydro-4-methylnaphthalene-1,3(2H,4H)-dione.

Workup

  1. temperatureunder reflux
  2. stirringthe mixture is stirred
  3. temperatureunder reflux overnight
  4. additionis added
  5. temperaturethe mixture is heated
  6. temperatureunder reflux for 4 hr
  7. customThe ethanol is removed by rotary evaporation
  8. dissolutionthe residue is dissolved in water
  9. washwashed with ether
  10. extractionextracted with ether
  11. customThe combined extracts are dried
  12. customthe solvent is removed

Sources & evidence

ORD record
ord-395828b73e014c2a8a7934969db5ff8e
Source dataset
uspto-grants-1990_05
Patent number
US04921526

Reaction notes

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