4-Methoxyphenol → HCID 12833251, compound

HRID 1703345Notes

Reaction equation

HRID 1703345 reaction equation
Cl[CH:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5](Cl)[N:4]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.[OH-:20].[K+].[H][H]>CS(C)=O.O>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:2]([O:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([O:20][C:16]3[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=3)[N:4]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 90154-MethoxyphenolHCID 14797Potassium HydroxideHCID 1741112-Chloro-6(dichloromethyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 12833251HCID 12833251, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 15.04 grams (g) (0.076 mole (m)) of 2-dichloromethyl-6-chloropyridine, 39.50 g (0.32 m) of p-methoxyphenol and 18.14 g (0.32 m) of potassium hydroxide in 100 milliliters (ml) of dimethylsulfoxide was heated, with stirring, for 72 hours. The resulting mixture was cooled to 25° C., diluted with water and extracted with 1,1,1-trichloroethane. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was subjected to Kugelrohr distillation removing as impurities any material boiling up to 200° C. at 0.05-1 millimeter of mercury (mm). The 2-[bis-(4-methoxyphenoxy)methyl]-6-(4-methoxyphenoxy)pyridine product was removed as the residue of the distillation and was a brown thick oil. The product was obtained in a yield of 25.3 g and upon analysis, was found to have carbon, hydrogen and nitrogen contents of 70.80, 5.37 and 3.09 percent, respectively, as compared with the theoretical contents of 70.59, 5.45 and 3.05 percent, respectively, as calculated for the above named compound.

Workup

  1. temperaturewas heated
  2. extractionextracted with 1,1,1-trichloroethane
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. distillationThe concentrate was subjected to Kugelrohr distillation
  7. customremoving as impurities any material
  8. customboiling up to 200° C. at 0.05-1 millimeter of mercury (mm)
  9. customThe 2-[bis-(4-methoxyphenoxy)methyl]-6-(4-methoxyphenoxy)pyridine product was removed as the residue of the distillation
  10. customThe product was obtained in a yield of 25.3 g and upon analysis

Sources & evidence

ORD record
ord-071fde58b3f94bc8b756f892b54af42e
Source dataset
uspto-grants-1982_09
Patent number
US04351943

Reaction notes

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