Sodium periodate → 2-Hexanone, 4-hydroxy-5-[4-[4-(trifluoromethyl)phenoxy]phenoxy]-

HRID 2417651Notes

Reaction equation

HRID 2417651 reaction equation
CN(C)N=[C:4]([CH2:6][CH:7]([OH:28])[CH:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[CH3:9])[CH3:5].I([O-])(=O)(=O)=[O:31].[Na+]>CO.P([O-])([O-])([O-])=O.O>[OH:28][CH:7]([CH:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[CH3:9])[CH2:6][C:4](=[O:31])[CH3:5]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 544292334-Hydroxy-5-[4-(4-trifluoromethylphenoxy)phenoxy]-2-hexanone N,N-dimethylhydrazone

Product 1

HCID 202783992-Hexanone, 4-hydroxy-5-[4-[4-(trifluoromethyl)phenoxy]phenoxy]-

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1061PhosphateSolvent

Procedure

4-Hydroxy-5-[4-(4-trifluoromethylphenoxy)phenoxy]-2-hexanone N,N-dimethylhydrazone (1 mmol) is dissolved in methanol (15 ml) and 1.0 N pH 7 phosphate buffer (3 ml), and a solution of sodium periodate (2.2 mmol) in water (5 ml) is added at 25° with stirring. After about 3 hours, the reaction mixture is filtered, poured into water and extracted with methylene chloride. The extract is dried and concentrated in vacuo to give 4-hydroxy-5-[4-(4-trifluoromethylphenoxy)phenoxy]-2-hexanone (cpd. 1, Table B).

Workup

  1. filtrationthe reaction mixture is filtered
  2. additionpoured into water
  3. extractionextracted with methylene chloride
  4. customThe extract is dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3084eb9acabe4f1c9dd5ca0b7eaa0b3c
Source dataset
uspto-grants-1984_09
Patent number
US04469872

Reaction notes

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