Isopropanol → HCID 12202658, compound

HRID 1448143Notes

Reaction equation

HRID 1448143 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.C(OO)(=[O:17])C.C(O)(C)C>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][C:6]1[CH:7]=[N+:8]([O-:17])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6585Peracetic AcidHCID 12202653HCID 12202653, compound

Product 1

HCID 12202658HCID 12202658, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 110 g of 3-(m-chlorophenoxy)pyridine [Agr. Biol. Chem., 34, 68 (1970)] at 35° C. in 125 ml of glacial acetic acid is treated with 112 g of 40% peracetic acid in acetic acid in four equal portions. The mixture is held at 27° C. for 16 hours and heated at reflux for 1 hour. The mixture is cooled to 70° C., 100 ml of isopropanol is added and the mixture is heated at 95° C. for 1 hour. The warm mixture is concentrated at reduced pressure, dissolved in 500 ml of dichloromethane and extracted with excess 25% sodium hydroxide solution. The dichloromethane is removed at reduced pressure and the 3-(m-chlorophenoxy)pyridine N-oxide is isolated by distillation; 150°-152° C. at 0.15 mm, mp 72°-75° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperaturethe mixture is heated at 95° C. for 1 hour
  4. concentrationThe warm mixture is concentrated at reduced pressure
  5. dissolutiondissolved in 500 ml of dichloromethane
  6. extractionextracted with excess 25% sodium hydroxide solution
  7. customThe dichloromethane is removed at reduced pressure

Sources & evidence

ORD record
ord-5c2cb0f45dfd4bebbb97bc62e4d3b8dc
Source dataset
uspto-grants-1979_12
Patent number
US04179563

Reaction notes

Loading…