Sulfuric Acid → Ethoxyethyl-2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoate

HRID 1156217Notes

Reaction equation

HRID 1156217 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[Cl:22])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O>CCOCCO>[CH2:8]([O:11][CH2:12][CH2:13][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][C:13]=2[Cl:22])[CH:9]=[CH:10][C:2]=1[Cl:1])[CH3:7]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 130136822-Chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid

Product 1

HCID 12799637Ethoxyethyl-2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoateYield 129.8%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent2×

Procedure

In 80 ml ethyl cellosolve was dissolved 2.0 g (0.0057 mol) of 2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid, and a catalytic amount of sulfuric acid was added. The mixture was heated to reflux for 8 hours. After stopping of the reaction, ethyl cellosolve was removed by distillation, and the residue was extracted with benzene. The extract was washed with a dilute aqueous solution of caustic soda and then with water, and dehydrated with sodium sulfate. By concentration 1.8 g (0.0037 mol) of the intended product was obtained; yield 65.2%, nD25 1.5272.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 hours
  3. customwas removed by distillation
  4. extractionthe residue was extracted with benzene
  5. washThe extract was washed with a dilute aqueous solution of caustic soda

Sources & evidence

ORD record
ord-084955507ca14125a3693f85ae650309
Source dataset
uspto-grants-1982_06
Patent number
US04334914

Reaction notes

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