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

HRID 255489

Reaction equation

HRID 255489 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.C[CH:24](O)[C:25]([O-:27])=[O:26].[C:29]1(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][CH2:24][C:25]([O:27][CH3:29])=[O:26])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 91435LactateHCID 13607437{3-[2-Chloro-4-(trifluoromethyl)phenoxy]phenyl}acetic acid

Product 1

HCID 13630152Methoxycarbonylmethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetateYield 726.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.3 g of 3-(2'-chloro-4'-trifluoromethylphenoxy) phenylacetic acid and 1 g of methylglycolate were dissolved in 50 ml of benzene. Then, 0.2 g of p-toluenesulfonic acid was added to the resulting solution, followed by heating under reflux for 3 hours. After completion of the reaction, 50 ml of ether was added. The resulting reaction mixture was washed with water according to the customary method and dehydrated with anhydrous sodium sulfate, and the solvent was distillend off under reduced pressure to obtain 3.4 g of methoxycarbonylmethyl 3-(2'-chloro-4'-trifluoromethylphenoxy)phenylacetate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. additionwas added
  4. customThe resulting reaction mixture
  5. washwas washed with water according to the customary method

Sources & evidence

ORD record
ord-ea1321671bf84374b811f91bf6d035e1
Source dataset
uspto-grants-1987_10
Patent number
US04698094

Linked notes

Loading…