Hydrochloric Acid → Ethyl 3,4-dichlorophenylacetate

HRID 224288Notes

Reaction equation

HRID 224288 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. additiondiluted with 200 ml of water and neutralized with concentrated ammonium hydroxide
  5. extractionThis aqueous mixture is extracted 3 times with chloroform
  6. concentrationConcentration and decolorization of the chloroform

Sources & evidence

ORD record
ord-291ab04acfd64a1e845e3da713d14741
Source dataset
uspto-grants-1980_11
Patent number
US04231935

Reaction notes

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