2-Chlorophenol → Ethyl 2-(2-chlorophenoxy)acetate

HRID 2072687Notes

Reaction equation

HRID 2072687 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Cl[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 72452-ChlorophenolHCID 7751Ethyl chloroacetateHCID 11430Potassium Carbonate

Product 1

HCID 302826Ethyl 2-(2-chlorophenoxy)acetateYield 80.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 51.4 g of o-chlorophenol, 58.8 g of ethyl chloroacetate, 55.3 g of potassium carbonate and 250 ml of acetone was heated under reflux for 7 hours. The mixture was then cooled to room temperature and an insoluble material was filtered off. The filtrate was concentrated in vacuo and the resulting residue was purified by silica gel column chromatography to give 69.0 g of the title compound as an oil, boiling at 134°-137° C./2 mm Hg (267 Pa).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. filtrationan insoluble material was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-97f4c36c523e4657b1aac72f02276512
Source dataset
uspto-grants-1990_04
Patent number
US04914093

Reaction notes

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