Ethyl Acetoacetate → HCID 13749118, compound

HRID 1732184Notes

Reaction equation

HRID 1732184 reaction equation
[Na].C(OCC)(=O)[CH2:3][C:4]([CH3:6])=[O:5].[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>[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24]2[CH2:25][CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:6][C:4](=[O:5])[CH:3]=2)[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 5360545SodiumHCID 53981476HCID 53981476, compound

Product 1

HCID 13749118HCID 13749118, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of sodium (1.21 g, 0.0526 mole) in ethanol (150 ml) and ethyl acetoacetate (6.85 g, 0.0526 moles) was added [2,3-dichloro-4-(1-oxo-3-phenyl-2-propenyl)phenoxy]acetic acid (8.7 g, 0.0248 mole)(Step A). The reaction mixture was heated at reflux for 3 hours, then the solvent was distilled at reduced pressure. The residue was dissolved in water, extracted with ether, acidified with hydrochloric acid, extracted with methylene chloride and ethyl acetate, dried over magnesium sulfate and evaporated at reduced pressure to give [2,3-dichloro-4-(5-phenyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 197°-199° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. distillationthe solvent was distilled at reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ether
  6. extractionextracted with methylene chloride and ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-2a1542ed0b704a21b8af759dbc9c2360
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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