Diethyl Ether → 1-Methyl-2-methoxyethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetate

HRID 255488Notes

Reaction equation

HRID 255488 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][CH:26](O)[CH3:27].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][CH:26]([CH3:27])[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 79001-Methoxy-2-propanolHCID 13607437{3-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl}acetic acid

Product 1

HCID 138490201-Methyl-2-methoxyethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetateYield 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.3 g of 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetic acid and 1.8 g of 1-methoxy-2-propanol 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 6 hours. After completion of the reation, 50 ml of ether was added to the reaction mixture. The resulting mixture was washed with water by the customary method and dehydrated with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 3.9 g of 1-methyl-2-methoxyethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetate.

Workup

  1. temperatureThen, the mixture was heated
  2. temperatureunder reflux for 6 hours
  3. washThe resulting mixture was washed with water by the customary method
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-664edf2ed25e48778f4b59b45357a0b4
Source dataset
uspto-grants-1987_10
Patent number
US04698094

Reaction notes

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