Hydrochloric Acid → Ethyl 3,4-dichlorophenylacetate

HRID 1903260Notes

Reaction equation

HRID 1903260 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH2:14](O)[CH3:15]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:14][CH3:15])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 798743,4-Dichlorophenylacetic acid

Product 1

HCID 2737422Ethyl 3,4-dichlorophenylacetate

Procedure

A solution of 59.5 g. of 3,4-dichlorophenylacetic acid in 500 ml. of absolute ethanol is saturated with anhydrous hydrogen chloride and then heated at reflux for 2 hours. The mixture is concentrated under reduced pressure to 200 ml., diluted with 200 ml. of water and neutralized with concentrated ammonium hydroxide. This aqueous mixture is extracted 3 times with chloroform. Concentration and decolorization of the chloroform extracts gives ethyl 3,4-dichlorophenylacetate as a yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. concentrationThe mixture is concentrated under reduced pressure to 200 ml
  4. addition, diluted with 200 ml
  5. extractionThis aqueous mixture is extracted 3 times with chloroform
  6. concentrationConcentration and decolorization of the chloroform

Sources & evidence

ORD record
ord-c37a2a3548374a059c7e2ceef42c2545
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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