3-Hydroxybenzoic Acid → 3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

HRID 1074641Notes

Reaction equation

HRID 1074641 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:16][C:17]=1Cl.[OH-].[K+]>CS(C)=O>[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:15]=[CH:16][C:17]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 74203-Hydroxybenzoic Acid2×HCID 94813,4-DichlorobenzotrifluorideHCID 14797Potassium Hydroxide

Product 1

HCID 916853-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Hydroxybenzoic acid is an important intermediate product for the preparation of plant protection agents. Thus, in accordance with U.S. Pat. No. 4,031,131, 3-hydroxybenzoic acid can be reacted with 3,4-dichlorobenzotrifluoride in methanolic solution and in the presence of potassium hydroxide and dimethyl sulphoxide, to give 3-(2-chloro-4-trifluoromethylphenoxy)-benzoic acid. Nitrating this benzoic acid with potassium nitrate in concentrated sulphuric acid then gives 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid which, according to U.S. Pat. No. 3,798,276, is an important herbicide.

Workup

  1. customfor the preparation of plant protection agents

Sources & evidence

ORD record
ord-747a126a100e462f9653fb21901a6c1c
Source dataset
uspto-grants-1983_07
Patent number
US04393234

Reaction notes

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