Isopropanol → HCID 20375999, compound

HRID 1448847Notes

Reaction equation

HRID 1448847 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([OH:18])(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-:18])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 12673485HCID 12673485, compound

Product 1

HCID 20375999HCID 20375999, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 74.3 g of 3-(2-chlorophenoxy)pyridine [Agr. Biol. Ghem., 34, 68 (1970)] in 75 ml of glacial acetic acid in three equal portions. The temperature is maintained at 35°-40° C. for 16 hours and 75 ml of isopropanol is added and the mixture is refluxed 1 hour. The mixture is concentrated at reduced pressure and the oil is dissolved in 500 ml of dichloromethane. The extract is washed with 25% sodium hydroxide solution, concentrated and distilled to yield 3-(2-chlorophenoxy)pyridine 1-oxide, bp 145°-160° C. at 0.15 mM, mp 60°-64° C.

Workup

  1. temperatureThe temperature is maintained at 35°-40° C. for 16 hours
  2. temperaturethe mixture is refluxed 1 hour
  3. concentrationThe mixture is concentrated at reduced pressure
  4. dissolutionthe oil is dissolved in 500 ml of dichloromethane
  5. washThe extract is washed with 25% sodium hydroxide solution
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-17d8f397cd4e41729fec249c3b0b43e7
Source dataset
uspto-grants-1980_02
Patent number
US04187379

Reaction notes

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