Ethyl Acetoacetate → [(2,3-Dichloro-5'-oxo[2',3',4',5'-tetrahydro[1,1'-biphenyl]]-4-yl)oxy]acetic acid

HRID 1732171Notes

Reaction equation

HRID 1732171 reaction equation
C[O-:2].[Na+].[Cl:4][C:5]1[C:15]([Cl:16])=[C:14]([C:17](=O)[CH2:18][CH2:19]N(C)C)[CH:13]=[CH:12][C:6]=1[O:7][CH2:8][C:9]([OH:11])=[O:10].[C:24](OCC)(=O)[CH2:25][C:26](C)=O>C(O)C>[Cl:4][C:5]1[C:15]([Cl:16])=[C:14]([C:17]2[CH2:26][CH2:25][CH2:24][C:19](=[O:2])[CH:18]=2)[CH:13]=[CH:12][C:6]=1[O:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 10942334Sodium MethoxideHCID 13749098HCID 13749098, compound

Product 1

HCID 13749102[(2,3-Dichloro-5'-oxo[2',3',4',5'-tetrahydro[1,1'-biphenyl]]-4-yl)oxy]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of sodium methoxide (0.5 g, 0.009 moles) in ethanol (40 ml) and ethyl acetoacetate (0.9 ml) was added [2,3-dichloro-4-(3-dimethylamino-1-oxopropyl)phenoxy]acetic acid (0.95 g, 0.0027 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 with ether, washed with water, dried over magnesium sulfate and evaporated at reduced pressure to give 50 mg of [2,3-dichloro-4-(3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 197°-198° C. after purification by thin layer chromatography on silica gel (CH2Cl2 :THF:methanol; 50:1:1).

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 with ether
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-0c3c1ca0c39b499784e8376795289a54
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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