Water → Ethoxyethoxyethoxyethyl-2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoate

HRID 1156215Notes

Reaction equation

HRID 1156215 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11]O)[CH3:2].[Cl:13][C:14]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:25]=2[Cl:34])=[CH:19][C:15]=1[C:16](Cl)=[O:17].[OH2:35]>N1C=CC=CC=1>[CH2:1]([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:17][C:16](=[O:35])[C:15]1[CH:19]=[C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:25]=2[Cl:34])[CH:21]=[CH:22][C:14]=1[Cl:13])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8190Triethylene glycol monoethyl etherHCID 127996322-Chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl chloride

Product 1

HCID 12799642Ethoxyethoxyethoxyethyl-2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoateYield 63.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 20 ml pyridine was dissolved 2.0 g (0.0167 mol) of triethylene glycol monoethyl ether, and while stirring at room temperature, 1.8 g (0.0049 mol) of 2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride was added. After 4-hour stirring, the reaction fluid was poured into 200 ml of water, and extracted with benzene. The extract was washed with a dilute aqueous solution of caustic soda and then with dilute hydrochloric acid. By concentration 1.4 g (0.0031 mol) of the intended product was obtained as a viscous oily substance, yield 63.3%, nD28 1.5175.

Workup

  1. stirringAfter 4-hour stirring
  2. extractionextracted with benzene
  3. washThe extract was washed with a dilute aqueous solution of caustic soda

Sources & evidence

ORD record
ord-78344c1726334d7d8ae6d43c5c905d20
Source dataset
uspto-grants-1982_06
Patent number
US04334914

Reaction notes

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