1,2-Dichloroethane → Ethyl benzoylacetate

HRID 1989797Notes

Reaction equation

HRID 1989797 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+].Cl.C(#N)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Cl-].[Zn+2].[Cl-]>[C:11]([CH2:7][C:8]([O:10][CH2:2][CH3:3])=[O:9])(=[O:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 7505BenzonitrileHCID 86617294Potassium ethylmalonate

Product 1

HCID 7170Ethyl benzoylacetateYield 75%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
90 °C

Procedure

To 100 □ of 1,2-dichloroethane were added 5.5 □ of benzonitrile, 7.2 g of zinc 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 acid 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 75% (7.6 g).

Workup

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

Sources & evidence

ORD record
ord-45934e01d91a49cb9462ce9b1839f454
Source dataset
uspto-grants-2010_01
Patent number
US07642356B2

Reaction notes

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