2-Methoxyethanol → Methoxyethyl-2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoate

HRID 1156214Notes

Reaction equation

HRID 1156214 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](Cl)=[O:5].[CH3:23][O:24][CH2:25][CH2:26][OH:27]>>[CH3:23][O:24][CH2:25][CH2:26][O:27][C:4](=[O:5])[C:3]1[CH:7]=[C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][C:13]=2[Cl:22])[CH:9]=[CH:10][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 80192-MethoxyethanolHCID 127996322-Chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl chloride

Product 1

HCID 12799636Methoxyethyl-2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoateYield 87%

Procedure

In 20 ml methyl cellosolve was heated 2.0 g (0.0054 mol) of 2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride to temperatures of 80°-120° C. for 3 hours with stirring. After methyl cellosolve was distilled off, the residue was extracted with benzene. The extract was washed with a dilute aqueous solution of caustic soda and with water, and then dehydrated by adding sodium sulfate. By vacuum concentration thereof 2.2 g (0.0047 mol) of the intended product was obtained as a viscous oily substance; yield 87.0%, nD25 1.5321.

Workup

  1. distillationAfter methyl cellosolve was distilled off
  2. extractionthe residue was extracted with benzene
  3. washThe extract was washed with a dilute aqueous solution of caustic soda and with water
  4. additionby adding sodium sulfate
  5. concentrationBy vacuum concentration

Sources & evidence

ORD record
ord-cba02c9ce4714b96b1a270c0b4ff2307
Source dataset
uspto-grants-1982_06
Patent number
US04334914

Reaction notes

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