Diethyl Ether → 2-Methoxyethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetate

HRID 255487Notes

Reaction equation

HRID 255487 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1.[CH3:23][O:24][CH2:25][CH2:26]O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOCC>C1C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:21])([F:20])[F:22])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([O:14][CH2:26][CH2:25][O:24][CH3:23])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 80192-MethoxyethanolHCID 13607437{3-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl}acetic acid

Product 1

HCID 136301602-Methoxyethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetateYield 100.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.3 g of 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetic acid and 1.5 g of 2-methoxyethanol were dissolved in 50 ml of benzene, followed by addition of 0.5 g of p-toluene sulfonic acid. Then, the mixture was heated under reflux for 3 hours. After completion of the reaction, to the reaction mixture was added 50 ml of ether. The resulting mixture was washed with water by the customary method and dried over anhydrous sodium sulfate, followed by evaporation-removal of the solvent under reduced pressure, thereby to obtain 3.9 g of 2-methoxyethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetate.

Workup

  1. temperatureThen, the mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter completion of the reaction
  4. washThe resulting mixture was washed with water by the customary method
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfollowed by evaporation-removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a105780859e34bd6b01f7bef9e829dcf
Source dataset
uspto-grants-1987_10
Patent number
US04698094

Reaction notes

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