Ethyl Acetoacetate → HCID 13749117, compound

HRID 1732182Notes

Reaction equation

HRID 1732182 reaction equation
C[O-].[Na+].C(OCC)(=O)[CH2:5][C:6]([CH3:8])=[O:7].[Cl:13][C:14]1[C:24]([Cl:25])=[C:23]([C:26](=O)[C:27](=[CH2:33])[CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH:22]=[CH:21][C:15]=1[O:16][CH2:17][C:18]([OH:20])=[O:19]>C(O)C>[Cl:13][C:14]1[C:24]([Cl:25])=[C:23]([C:26]2[CH:27]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:33][CH2:8][C:6](=[O:7])[CH:5]=2)[CH:22]=[CH:21][C:15]=1[O:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 10942334Sodium MethoxideHCID 20226829HCID 20226829, compound

Product 1

HCID 13749117HCID 13749117, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of sodium methoxide (2.3 g, 0.043 mole) in ethanol (50 ml) and ethyl acetoacetate (5.56 g, 0.043 mole) was added [2,3-dichloro-4-(2-methylene-2-cyclopentyl-1-oxoethyl)phenoxy]acetic acid (6.5 g, 0.019 mole). The reaction mixture was heated at reflux for 2 hours, then the solvent was distilled at reduced pressure. The residue was dissolved in water, acidified, extracted into ether, washed with water, extracted into sodium bicarbonate, acidified, extracted into ether, washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give 2.6 g of [2,3-dichloro-4-(6-cyclopentyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 206°-207° C. after recrystallization from 300 ml of toluene.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. distillationthe solvent was distilled at reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted into ether
  6. washwashed with water
  7. extractionextracted into sodium bicarbonate
  8. extractionextracted into ether
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b78a2f3a4ba34a2f955c70da8d3734f1
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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