Ethyl 3-phenylprop-2-enoate → Ethyl 2,4-dioxo-6-phenylcyclohexane-1-carboxylate

HRID 1973504Notes

Reaction equation

HRID 1973504 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[C:10](OCC)(=[O:19])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[O-]CC.[Na+]>[O:4]=[C:3]1[CH2:5][C:10](=[O:19])[CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]1[C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 7649Ethyl 3-phenylprop-2-enoateHCID 8868Ethyl Acetoacetate

Product 1

HCID 12617805Ethyl 2,4-dioxo-6-phenylcyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

To a cooled solution of sodium ethoxide (from 2.3 g. sodium and absolute ethanol, 30 ml.) was added with shaking ethyl acetoacetate (13 g.). When homogeneous the mixture was treated with ethyl cinnamate (17.8 g.) and then heated under reflux for 18 hrs. After cooling the solution, the precipitated enolate salt (formula III) was collected by filtration and washed with acetone. Dissolution in cold water, followed by acidification with 2N-sulphuric acid (to convert the enolate salt to the corresponding dione II) afforded crystalline ethyl 2,4-dioxo-6-phenylcyclohexanecarboxylate.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hrs
  3. temperatureAfter cooling the solution
  4. filtrationthe precipitated enolate salt (formula III) was collected by filtration
  5. washwashed with acetone
  6. dissolutionDissolution in cold water

Sources & evidence

ORD record
ord-f1ccac4b83c744aa8703befe0563ed02
Source dataset
uspto-grants-1976_12
Patent number
US03997590

Reaction notes

Loading…