Ethyl cyanoacetate → HCID 20144393, compound

HRID 648945Notes

Reaction equation

HRID 648945 reaction equation
[Na].[C:2]([CH2:4][C:5]([O:7]CC)=O)#[N:3].[O:10]=[C:11]([CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:12]>C(O)C>[C:2]([CH:4]1[C:14]([CH3:16])([CH3:15])[CH2:13][C:11](=[O:10])[CH2:12][C:5]1=[O:7])#[N:3]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8858Mesityl oxideHCID 5360545Sodium

Product 1

HCID 20144393HCID 20144393, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (11.5 g, 0.5 mol) was dissolved in dry ethanol (225 ml) at ambient temperature (20° C.). Ethyl cyanoacetate (60 g, 0.53 mol) was added dropwise with stirring at ambient temperature. To the resulting solution was added dropwise, with stirring, mesityl oxide, and the mixture was heated under reflux for 4 hours. After cooling, the mixture was extracted with diethyl ether to remove any unreacted starting material and acidified with 2M aqueous hydrochloric acid. The brown oil which separated out was extracted into diethyl ether, dried (Na2SO4) evaporated and triturated with 40°-60° C. petroleum ether to give a pale yellow solid, which on recrystallisation from diethyl ether gave 4-cyano-5,5-dimethyl-1,3-cyclohexanedione as a white crystalline solid (48.6 g, 58.9%) m.p. 130°-132° C.

Workup

  1. additionTo the resulting solution was added dropwise
  2. stirringwith stirring
  3. temperatureunder reflux for 4 hours
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with diethyl ether
  6. customto remove
  7. customThe brown oil which separated out
  8. extractionwas extracted into diethyl ether
  9. dry with materialdried (Na2SO4)
  10. customevaporated
  11. customtriturated with 40°-60° C. petroleum ether
  12. customto give a pale yellow solid, which
  13. customon recrystallisation from diethyl ether

Sources & evidence

ORD record
ord-14cd01ffb0dd48cdbbb8144df240a513
Source dataset
uspto-grants-1988_04
Patent number
US04737507

Reaction notes

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