Water → HCID 14053357, compound

HRID 652064Notes

Reaction equation

HRID 652064 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].[OH-].[K+].O.[Cl:16][C:17]1[CH:18]=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:20]=[CH:21][C:22]=1Cl>C1(C)C=CC=CC=1.CS(C)=O.[Cu].[I-].[K+]>[Cl:16][C:17]1[CH:18]=[C:19]([C:24]([F:25])([F:26])[F:27])[CH:20]=[CH:21][C:22]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6]

Participants

9

Reactant 4

HCID 962WaterHCID 94813,4-DichlorobenzotrifluorideHCID 12575Isovanillic AcidHCID 14797Potassium Hydroxide

Product 1

HCID 14053357HCID 14053357, compoundYield 83.6%

Reagents, catalysts & solvents 4

HCID 4875Potassium IodideCatalystHCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 33.6 g (0.2 mol) of 3-hydroxy-4-methoxybenzoic acid and 26.8 g (0.4 mol) of potassium hydroxide (85%) in 200 ml of toluene and 200 ml of dimethyl sulfoxide is dewatered at 140° C. in a sulfonating flask equipped with a water separator. The toluene is distilled off and the mixture is then cooled to 90° C. and 43 g (0.2 mol) of 3,4-dichlorobenzotrifluoride, 1.1 g of potassium iodide and 0.2 g of copper filings in 20 ml of dimethyl sulfoxide are added. The mixture is kept for 30 hours at 150° C. and the solvent is then distilled off under a high vacuum. The residue is dissolved in 250 ml of water, the solution is filtered, the filtrate is acidified with 100 ml of 2N HCl in 200 g of ice and the precipitate obtained is filtered with suction, then washed with water and vacuum-dried at 80° C., affording 58 g of 3-(2-chloro-4-trifluoromethylphenoxy)-4-methoxybenzoic acid. Melting point 162°-165° C.

Workup

  1. customis dewatered at 140° C. in a sulfonating flask
  2. distillationThe toluene is distilled off
  3. distillationthe solvent is then distilled off under a high vacuum
  4. dissolutionThe residue is dissolved in 250 ml of water
  5. filtrationthe solution is filtered
  6. customthe precipitate obtained
  7. filtrationis filtered with suction
  8. washwashed with water
  9. customvacuum-dried at 80° C.

Sources & evidence

ORD record
ord-e0e6e747835745258c6afbb8ec573f95
Source dataset
uspto-grants-1987_06
Patent number
US04670441

Reaction notes

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