Ethanol → HCID 13749105, compound

HRID 1732174Notes

Reaction equation

HRID 1732174 reaction equation
[Na].[C:2](OCC)(=O)[CH2:3][C:4](C)=O.[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24](=O)[CH:25]=[CH:26][CH3:27])[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17].C([OH:31])C>>[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24]2[CH2:2][CH:3]([CH3:4])[CH2:27][C:26](=[O:31])[CH:25]=2)[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 8868Ethyl AcetoacetateHCID 5360545SodiumHCID 53828567HCID 53828567, compound

Product 1

HCID 13749105HCID 13749105, compound

Procedure

To a stirred solution of sodium (0.836 g, 0.0363 mole) in ethanol (70 ml) and ethyl acetoacetate (4.73 g, 0.0363 mole) was added [2,3-dichloro-4-(1-oxo-2-butenyl)phenoxy]acetic acid (4.67 g, 0.0162 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, dried over magnesium sulfate and evaporated at reduced pressure to give 3.7 g of [2,3-dichloro-4-(5-methyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 187°-190° C. after recrystallization from acetonitrile.

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. dry with materialdried over magnesium sulfate
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-f1c3691d208e4f189de98db47c0598a4
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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