Methanol → 4-Chloro-2-(3-trifluoromethylphenoxy)-benzoic acid methyl ester

HRID 2419298Notes

Reaction equation

HRID 2419298 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH:3]=1.S(=O)(=O)(O)O.[CH3:27]O>>[CH3:27][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 227678684-Chloro-2-(3-trifluoromethyl-phenoxy)-benzoic acid

Product 1

HCID 540086294-Chloro-2-(3-trifluoromethylphenoxy)-benzoic acid methyl ester

Procedure

136 G. of 4-chloro-2-(3-trifluoromethyl-phenoxy)-benzoic acid are boiled at reflux for 2.5 hours in a mixture of 1000 ml. of methanol and 100 ml. of concentrated sulfuric acid. After concentration of the mixture under vacuum, the residue is poured on to ice and extracted with benzene. The benzene extracts are washed with water, aqueous sodium bicarbonate solution and again with water. After evaporation of the benzene, there is obtained 4-chloro-2-(3-trifluoromethylphenoxy)-benzoic acid methyl ester in the form of an oil.

Workup

  1. temperatureat reflux for 2.5 hours in a mixture of 1000 ml
  2. additionAfter concentration of the mixture under vacuum, the residue is poured on to ice
  3. extractionextracted with benzene
  4. washThe benzene extracts are washed with water, aqueous sodium bicarbonate solution and again with water
  5. customAfter evaporation of the benzene

Sources & evidence

ORD record
ord-1b3e2021028e48f4ab21768790261cd8
Source dataset
uspto-grants-1978_08
Patent number
US04105664

Reaction notes

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