Methyl acetoacetate → HCID 21491897, compound

HRID 1973502Notes

Reaction equation

HRID 1973502 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH3:9][C:10]1[CH:22]=[CH:21][C:13]([CH:14]=[CH:15][C:16](OCC)=[O:17])=[CH:12][CH:11]=1>C[O-].[Na+]>[O:4]=[C:3]1[CH2:5][C:16](=[O:17])[CH2:15][CH:14]([C:13]2[CH:12]=[CH:11][C:10]([CH3:9])=[CH:22][CH:21]=2)[CH:2]1[C:1]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 334099Ethyl 3-(4-methylphenyl)-2-propenoate

Product 1

HCID 21491897HCID 21491897, compound

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

To a cooled solution of sodium methoxide (from 2.3 g., sodium and absolute methanol, 40 ml.) was added with shaking methyl acetoacetate (11.8 g.). When homogeneous the mixture was treated with ethyl p-methylcinnamate (19. g.) and then heated under reflux for 18 hrs. After cooling the precipitated sodium enolate salt (formula III) was collected by filtration and washed with acetone. This enolate salt was then converted to the corresponding dione of formula II by dissolving in cold water followed by acidification with 2-N-hydrochloric acid, which afforded crystalline methyl 2,4-dioxo-6-p-tolylcyclohexanecarboxylate.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hrs
  3. filtrationwas collected by filtration
  4. washwashed with acetone
  5. dissolutionby dissolving in cold water

Sources & evidence

ORD record
ord-cc40106f27a548deb0543244bd0565b4
Source dataset
uspto-grants-1976_12
Patent number
US03997590

Reaction notes

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