Isopropanol → HCID 20375999, compound

HRID 1448144Notes

Reaction equation

HRID 1448144 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.C(OO)(=[O:17])C.C(O)(C)C>C(O)(=O)C>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N+:7]([O-:17])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6585Peracetic AcidHCID 12673485HCID 12673485, compound

Product 1

HCID 20375999HCID 20375999, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 74.3 g of 3-(o-chlorophenoxy)pyridine [Agr. Biol. Chem. 34, 68 (1970)] in 75 ml of glacial acetic acid at 35° C. is treated with 76 g of 40% peractic acid in acetic acid in three equal portions. The mixture is held at 35° C. for 16 hours, refluxed 1 hour, cooled to 60° C. and 75 ml of isopropanol is added. The mixture is refluxed for 1 hour, cooled and concentrated at reduced pressure. The oil is dissolved in 700 ml of dichloromethane, washed with excess 25% sodium hydroxide solution, concentrated at reduced pressure and distilled to yield 3-(o-chlorophenoxy)pyridine N-oxide, bp 150°-155° C. at 0.15 mm.

Workup

  1. temperaturerefluxed 1 hour
  2. temperatureThe mixture is refluxed for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated at reduced pressure
  5. dissolutionThe oil is dissolved in 700 ml of dichloromethane
  6. washwashed with excess 25% sodium hydroxide solution
  7. concentrationconcentrated at reduced pressure
  8. distillationdistilled

Sources & evidence

ORD record
ord-9b1e09ff9a61432a80b4dd617f0d0768
Source dataset
uspto-grants-1979_12
Patent number
US04179563

Reaction notes

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