Isopropanol → HCID 23335425, compound

HRID 903861Notes

Reaction equation

HRID 903861 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.C(OO)(=[O:18])C.C(O)(C)C>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][C:7]1[CH:8]=[N+:9]([O-:18])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6585Peracetic AcidHCID 12673488HCID 12673488, compound

Product 1

HCID 23335425HCID 23335425, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
35 °C

Procedure

A solution of 68 g of 3-(3-methoxyphenoxy)pyridine in 100 ml of glacial acetic acid is treated with 75 g of 40% peracetic acid in acetic acid. The mixture is stirred 16 hours at 35° C. and then is refluxed 1 hour. The mixture is cooled, 100 ml isopropanol added, and the mixture is concentrated at reduced pressure. The oily residue is dissolved in 500 ml of dichloromethane and is washed with excess cold 25% sodium hydroxide solution. The organic layer is concentrated to yield 3-(3-methoxyphenoxy)pyridine 1-oxide, m.p. 75°-77° C.

Workup

  1. temperatureis refluxed 1 hour
  2. temperatureThe mixture is cooled
  3. concentrationthe mixture is concentrated at reduced pressure
  4. dissolutionThe oily residue is dissolved in 500 ml of dichloromethane
  5. washis washed with excess cold 25% sodium hydroxide solution
  6. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-1fbbb450ceaf42f2b079c7a4687fa688
Source dataset
uspto-grants-1980_10
Patent number
US04229457

Reaction notes

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