Ethanol → HCID 13749103, compound

HRID 1732172Notes

Reaction equation

HRID 1732172 reaction equation
[CH3:1][O-].[Na+].[Cl:4][C:5]1[C:15]([Cl:16])=[C:14]([C:17](=O)[C:18](=[CH2:20])[CH3:19])[CH:13]=[CH:12][C:6]=1[O:7][CH2:8][C:9]([OH:11])=[O:10].[CH2:22]([OH:24])[CH3:23]>C(OCC)(=O)CC(C)=O>[Cl:4][C:5]1[C:15]([Cl:16])=[C:14]([C:17]2[CH:18]([CH3:20])[CH2:19][CH2:1][C:22](=[O:24])[CH:23]=2)[CH:13]=[CH:12][C:6]=1[O:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 10942334Sodium MethoxideHCID 12395520HCID 12395520, compound

Product 1

HCID 13749103HCID 13749103, compound

Reagents, catalysts & solvents 1

HCID 8868Ethyl AcetoacetateSolvent

Procedure

To a stirred solution of sodium methoxide (2.0 g, 0.037 mole) in ethanol (60 ml) and ethyl acetoacetate (4.86 ml) was added [2,3-dichloro-4-(2-methylene-1-oxopropyl)phenoxy]acetic acid (4.8 g, 0.017 mole). The reaction mixture was heated at reflux for 3 hours then the solvent was distilled at reduced pressure. The residue was dissolved in water, acidified with hydrochloric acid, extracted with ether, washed with water, extracted in sodium bicarbonate and acidified to get a precipitate which was filtered, rinsed with water, dried, and recrystallized from 500 ml toluene to give 2,3-dichloro-4-(6-methyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 185° 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. washwashed with water
  7. extractionextracted in sodium bicarbonate
  8. customto get a precipitate which
  9. filtrationwas filtered
  10. washrinsed with water
  11. customdried
  12. customrecrystallized from 500 ml toluene
  13. customto give 2,3-dichloro-4-(6-methyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 185° C.

Sources & evidence

ORD record
ord-7132d7621f2e4f41b97f0547a558a289
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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