Hydrochloric Acid → 4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenol

HRID 261738Notes

Reaction equation

HRID 261738 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Cl[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1.[OH-].[K+].Cl>CS(C)=O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 1552414-(5-Trifluoromethyl-pyridin-2-yloxy)-phenolYield 35.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

40 ml of dimethyl sulfoxide, 4.2 g of hydroquinone, 5.0 g of 2-chloro-5-trifluoromethylpyridine and 2.3 g of potassium hydroxide were reacted at 150° C. for 2 hours with stirring in a nitrogen atmosphere. After the reaction product was allowed to cool, the product was added to a suitable amount of ice-water, neutralized with 30% concentrated hydrochloric acid, and extracted with methylene chloride. The extract was washed with water and dried over anhydrous sodium sulfate. 2.5 g of 2-(4-hydroxyphenoxy)-5-trifluoromethylpyridine (m.p. 82°-84° C.) was obtained by distilling off the methylene chloride.

Workup

  1. temperatureto cool
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-b8ec36cb5f60470cad4e3846f7c0ba9b
Source dataset
uspto-grants-1979_05
Patent number
US04152328

Reaction notes

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