1,2-Dichloroethane → Ethyl benzoylacetate

HRID 1989798Notes

Reaction equation

HRID 1989798 reaction equation
Cl[CH2:2][CH2:3]Cl.C([CH:7]([C:11]([O-:13])=O)[C:8]([O-:10])=[O:9])C.[K+].[K+].C(#N)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Cu](Cl)Cl>[C:11]([CH2:7][C:8]([O:10][CH2:2][CH3:3])=[O:9])(=[O:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 7505BenzonitrileHCID 86617294Potassium ethylmalonate

Product 1

HCID 7170Ethyl benzoylacetateYield 68%

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Conditions

Temperature
90 °C

Procedure

To 100 □ of 1,2-dichloroethane were added 5.5 □ of benzonitrile, 3.6 g of copper chloride and 11 g of potassium ethylmalonate, and then the mixture was stirred at reflux. After the reaction was completed, 100 □ of 6 N hydrochloric was added to the mixture, which then was stirred at reflux at 90° C. for 1 hour. After confirming completion of the reaction by TLC, the solution was cooled to 20° C., and then an organic layer was separated therefrom. The organic layer was concentrated through distillation under reduced pressure. Thus resulted residue was purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=1/20, v/v) to obtain the title compound in the yield of 68% (7.0 g).

Workup

  1. temperatureat reflux
  2. addition100 □ of 6 N hydrochloric was added to the mixture, which
  3. stirringthen was stirred
  4. customcompletion of the reaction by TLC
  5. temperaturethe solution was cooled to 20° C.
  6. customan organic layer was separated
  7. concentrationThe organic layer was concentrated through distillation under reduced pressure
  8. customThus resulted residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-91b9e7e280524cada39b751ba1498914
Source dataset
uspto-grants-2010_01
Patent number
US07642356B2

Reaction notes

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