Ethacrynic Acid → [2,3-Dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid

HRID 1732177Notes

Reaction equation

HRID 1732177 reaction equation
[CH3:1][O-].[Na+].C(OCC)(=O)[CH2:5][C:6](C)=[O:7].[Cl:13][C:14]1[C:24]([Cl:25])=[C:23]([C:26](=O)[C:27](=[CH2:30])[CH2:28][CH3:29])[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]([CH2:30][CH3:1])[CH2:28][CH2:29][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 3278Ethacrynic AcidHCID 8868Ethyl AcetoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 10759778[2,3-Dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of sodium methoxide (24.3 g, 0.45 mole) in ethanol (700 ml) and ethyl acetoacetate (58.6 g, 0.45 mole) was added [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid (60.6 g, 0.20 mole). The reaction mixture was heated at reflux for 21/2 hours, then the solvent was distilled at reduced pressure. The residue was dissolved in water, acidified with hydrochloric acid, extracted into ether, washed with water, extracted into sodium bicarbonate, acidified, extracted into ether, dried over magnesium sulfate, filtered and evaporated in vacuo to give 68 g of [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melts at 170°-172° after recrystallization from nitromethane.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 21/2 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. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-aa290589aea34ba08f05ff1c41c4111c
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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