Phenol → HCID 12833242, compound

HRID 1702861Notes

Reaction equation

HRID 1702861 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8](Cl)Cl)[N:3]=1.[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-:18].[K+]>CS(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([O:18][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 1741112-Chloro-6(dichloromethyl)pyridine

Product 1

HCID 12833242HCID 12833242, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 25 grams (g) (0.13 mole (m)) of 2-chloro-6-(dichloromethyl)pyridine, 29.91 g (0.32 m) of phenol and 17.84 g (0.32 m) of potassium hydroxide in 100 milliliters (ml) of dimethylsulfoxide was heated, with stirring, for 6 hours at 70° C. The reaction mixture was cooled, 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 and 27.3 g of a yellow viscous liquid was recovered. This liquid was determined to be the desired 2-chloro-6-(diphenoxymethyl)pyridine by its nuclear magnectic resonance spectra and its elemental analysis. The product boiled at 150° C. at 0.1 millimeter of mercury (mm) and had a refractive index of nD25 =1.5991. The elemental analysis showed the product to have carbon, hydrogen and nitrogen contents of 68.63, 4.40 and 4.49 percent, respectively, as compared with the theoretical contents of 69.34, 4.49 and 4.49 percent, respectively, as calculated for the above named compound.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with 1,1,1-trichloroethane
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. distillationThe concentrate was subjected to Kugelrohr distillation and 27.3 g of a yellow viscous liquid
  8. customwas recovered

Sources & evidence

ORD record
ord-f033f14dc0bf49cbacf75aada9eb4049
Source dataset
uspto-grants-1982_09
Patent number
US04349680

Reaction notes

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