4-Methoxyphenol → 4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenol

HRID 261739Notes

Reaction equation

HRID 261739 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][CH:4]=1.ClC1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=1.[OH-].[K+]>CS(C)=O>[OH:7][C:6]1[CH:8]=[CH:9][C:3]([O:2][C:1]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 14797Potassium HydroxideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 1552414-(5-Trifluoromethyl-pyridin-2-yloxy)-phenolYield 29.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

40 ml of dimethyl sulfoxide, 5.0 g of hydroquinone monomethyl ether, 5.0 g of 2-chloro-5-trifluoromethylpyridine and 2.3 g of potassium hydroxide were reacted at 150° C. for 3 hours with stirring. After cooling, the reaction product was added to a suitable amount of ice-water, and extracted with methylene chloride. The extract was washed with water and dried over anhydrous sodium sulfate, followed by distilling off the methylene chloride. The residue containing 2-(4-methoxyphenoxy)-5-trifluoromethylpyridine was mixed with 5.0 g of pyridine hydrochloride and heated at 140°-160° C. for 2 hours with stirring. After cooling the system, the reaction product was added to a suitable amount of ice-water and extracted with methylene chloride. This methylene chloride layer was back-extracted with a 5% sodium hydroxide aqueous solution, and the extract was acidified with 30% concentrated hydrochloric acid to obtain a solid material. This solid material was filtered out and dried to obtain 2.1 g of 2-(4-hydroxyphenoxy)-5-trifluoromethylpyridine.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationby distilling off the methylene chloride
  6. additionThe residue containing 2-(4-methoxyphenoxy)-5-trifluoromethylpyridine
  7. additionwas mixed with 5.0 g of pyridine hydrochloride
  8. temperatureheated at 140°-160° C. for 2 hours
  9. stirringwith stirring
  10. temperatureAfter cooling the system
  11. additionthe reaction product was added to a suitable amount of ice-water
  12. extractionextracted with methylene chloride
  13. extractionThis methylene chloride layer was back-extracted with a 5% sodium hydroxide aqueous solution
  14. customto obtain a solid material
  15. filtrationThis solid material was filtered out
  16. customdried

Sources & evidence

ORD record
ord-13345add4040412e85619c7b86e698c9
Source dataset
uspto-grants-1979_05
Patent number
US04152328

Reaction notes

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