Sodium periodate → 4-Hydroxy-5-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-2-hexanone

HRID 1248094Notes

Reaction equation

HRID 1248094 reaction equation
CN(C)N=[C:4]([CH2:6][CH:7]([OH:29])[CH:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[C:23]([Cl:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[CH:20][N:19]=2)=[CH:13][CH:12]=1)[CH3:9])[CH3:5].I([O-])(=O)(=O)=[O:32].[Na+]>CO.P([O-])([O-])([O-])=O.O>[OH:29][CH:7]([CH:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[C:23]([Cl:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[CH:20][N:19]=2)=[CH:13][CH:12]=1)[CH3:9])[CH2:6][C:4](=[O:32])[CH3:5]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 736742964-hydroxy-5-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-2-hexanone N,N-dimethylhydrazone

Product 1

HCID 202784244-Hydroxy-5-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-2-hexanone

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1061PhosphateSolvent

Procedure

The above hexanone hydrazone (1 mmol) is dissolved in 10 ml of methanol with 2 ml of 2M pH 7 phosphate buffer, and a solution of sodium periodate (2.2 mmol) in 2 ml of water is added, with stirring. The mixture is stirred for 3 hours, after which the solvent is removed and the residue is extracted with chloroform. The extract is washed with water and dried and the solvent is removed to give 4-hydroxy-5-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-2-hexanone (C'; Q1 is N, Y is chloro, Z is trifluoromethyl, R1 is methyl and R2 is methyl).

Workup

  1. stirringThe mixture is stirred for 3 hours
  2. customafter which the solvent is removed
  3. extractionthe residue is extracted with chloroform
  4. washThe extract is washed with water
  5. customdried
  6. customthe solvent is removed

Sources & evidence

ORD record
ord-8439129490984acf833168317fabe439
Source dataset
uspto-grants-1985_06
Patent number
US04522647

Reaction notes

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