Water → HCID 53788847, compound

HRID 977064Notes

Reaction equation

HRID 977064 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][O:15][N:16]=[C:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[CH2:18][OH:19].C(O)(C)C.O>CC(C)=O>[CH3:14][O:15][N:16]=[C:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[C:18]([OH:3])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 53967011HCID 53967011, compoundHCID 131709961Jones' reagent

Product 1

HCID 53788847HCID 53788847, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 ml of Jones reagent (chromic anhydride in dilute sulfuric acid) were added to a solution in acetone of 0.40 g of 2'-chloro-2-hydroxyacetophenone O-methyloxime (the less polar isomer prepared above). The resulting mixture was stirred at room temperature for an hour and then 10 ml of isopropanol were added to it with ice-cooling. The reaction mixture was poured into 100 ml of water and extracted three times with 10 ml portions of ethyl acetate. The combined extracts were washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off to give 320 mg (75%) of the title compound as a crude product.

Workup

  1. customprepared above)
  2. temperaturecooling
  3. extractionextracted three times with 10 ml portions of ethyl acetate
  4. washThe combined extracts were washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-fe2ddd40cdd24ce1aadbaf0420b0d747
Source dataset
uspto-grants-1997_03
Patent number
US05614470

Reaction notes

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