Ethyl Acetoacetate → HCID 20155632, compound

HRID 2413841Notes

Reaction equation

HRID 2413841 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Na].[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24](=O)[CH:25]=[CH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17]>C(O)C>[C:16]([CH2:15][O:14][C:13]1[CH:19]=[CH:20][C:21]([C:24]2[CH2:25][CH:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:2]([C:1]([O:7][CH2:8][CH3:9])=[O:6])[C:3](=[O:4])[CH:5]=2)=[C:22]([Cl:23])[C:12]=1[Cl:11])([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 5360545SodiumHCID 53981476HCID 53981476, compound

Product 1

HCID 20155632HCID 20155632, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl acetoacetate (6.85 g, 0.0526M) was added at 70° to a solution of sodium (1.21 g, 0.0526M) dissolved in ethanol (150 ml). After a few minutes [2,3-dichloro-4-(3-phenyl-1-oxo-2-propenyl)phenoxy]acetic acid (8.7 g, 0.0248M) was added and the suspension was stirred at reflux for 3 hours, cooled and concentrated under vacuum. The residue was taken up in water, acidified with hydrochloric acid and extracted with methylene chloride. The organic extracts were washed with water dried over MgSO4 and concentrated. The residue was triturated with toluene and the solid that crystallized filtered. The crude product was taken up in butyl chloride and filtered. The filtrate was concentrated under vacuum and the residue recrystallized from toluene to give ethyl 4-[4-(carboxymethoxy)-2,3-dichlorophenyl]-2-oxo-6-phenyl-3-cyclohexene-1-carboxylate, m.p. 91° C.

Workup

  1. temperatureat reflux for 3 hours
  2. temperaturecooled
  3. concentrationconcentrated under vacuum
  4. extractionextracted with methylene chloride
  5. washThe organic extracts were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was triturated with toluene
  9. customthe solid that crystallized
  10. filtrationfiltered
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated under vacuum
  13. customthe residue recrystallized from toluene

Sources & evidence

ORD record
ord-6caaf6c2bd4f422bb97d1754f152f2b4
Source dataset
uspto-grants-1988_01
Patent number
US04719310

Reaction notes

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