Catechol → Phenol, 2-[(6-chloro-3-pyridazinyl)oxy]-

HRID 649503Notes

Reaction equation

HRID 649503 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[C:9]1([C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[OH:12])[OH:10].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CS(C)=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([O:10][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[OH:12])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 289CatecholHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 673313,6-Dichloropyridazine

Product 1

HCID 10421126Phenol, 2-[(6-chloro-3-pyridazinyl)oxy]-Yield 60.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

14.9 g of 3,6-dichloropyridazine and 14.3 g of catechol are dissolved in 40 ml of dimethyl sulfoxide, followed by addition of 15.2 g of anhydrous potassium carbonate. The mixture is heated gradually, and stirred at 80° to 90° C. for 2 hours. The reaction mixture, after cooling down, is poured into 300 ml of a 10% aqueous solution of sodium hydroxide. The resulting insoluble precipitates are filtered off and the filtrate is neutralized with concentrated hydrochloric acid. After the resulting crystals are filtrated, followed by drying to yield 13.4 g of title compound. When this product is subjected to treatment with activated charcoal and recrystallized from acetone, to yield colorless crystals of the title compound melting at 146.5°-148° C.

Workup

  1. temperatureThe mixture is heated gradually
  2. temperatureThe reaction mixture, after cooling down
  3. customThe resulting insoluble precipitates
  4. filtrationare filtered off
  5. filtrationAfter the resulting crystals are filtrated
  6. customby drying

Sources & evidence

ORD record
ord-aac8ec5e75a14eb79869ec3d1751672e
Source dataset
uspto-grants-1988_04
Patent number
US04740505

Reaction notes

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