Isopropanol → HCID 53828689, compound

HRID 1448138Notes

Reaction equation

HRID 1448138 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.C(OO)(=[O:17])C.C(O)(C)C>C(O)(=O)C>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]2[CH:8]=[N+:9]([O-:17])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6585Peracetic AcidHCID 12673486HCID 12673486, compound

Product 1

HCID 53828689HCID 53828689, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 93 g of 3-(p-chlorophenoxy)pyridine [Agr. Biol. Chem. 34, 68 (1970)] in 100 ml of glacial acetic acid is treated with 95 g of 40% peracetic acid in acetic acid in four equal portions. The mixture is heated at 35°-40° C. for 16 hours and than refluxed 1 hour. The mixture is cooled to 70° C., 100 ml of isopropanol is added and the reaction heated at 95° C. for 2 hours. The mixture is concentrated in vacuo and dissolved in 700 ml of dichloromethane. The solution is washed with 25 ml of 25% cold sodium hydroxide solution, dried over anhydrous MgSO4, concentrated at reduced pressure to yield crystalline 3-(p-chlorophenoxy)pyridine N-oxide, recrystallized from toluene; mp 138°-140° C.

Workup

  1. temperatureThe mixture is heated at 35°-40° C. for 16 hours
  2. temperaturethan refluxed 1 hour
  3. temperaturethe reaction heated at 95° C. for 2 hours
  4. concentrationThe mixture is concentrated in vacuo
  5. dissolutiondissolved in 700 ml of dichloromethane
  6. washThe solution is washed with 25 ml of 25% cold sodium hydroxide solution
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-4eccd579e8a645c2b5b5cf69479c74ba
Source dataset
uspto-grants-1979_12
Patent number
US04179563

Reaction notes

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