Acetone → HCID 14771334, compound

HRID 476740Notes

Reaction equation

HRID 476740 reaction equation
CC(C)=O.[OH:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>O>[O:5]=[C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 180AcetoneHCID 3776IsopropanolHCID 14771333HCID 14771333, compoundHCID 131709961Jones' reagent

Product 1

HCID 14771334HCID 14771334, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 ml of an acetone solution containing 0.50 g of N-[2-(2-hydroxycyclohexyloxy)phenyl]methanesulfonamide was added 0.5 g of 8N Jones reagent (chromic acid-sulfuric acid) under ice cooling with stirring, and the mixture was stirred for 1 hour. Then, to the reaction solution was added 1 ml of isopropyl alcohol and water, and the mixture was extracted with dichloromethane. The dichloromethane layer was washed, in turn, with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent; n-hexane:dichloromethane=1:1) and then recrystallized from ethanol-n-hexane to give 0.21 g of N-[2-(2-oxocyclohexyloxy)phenyl]methanesulfonamide.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe dichloromethane layer was washed, in turn, with water
  4. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (eluent; n-hexane:dichloromethane=1:1)
  7. customrecrystallized from ethanol-n-hexane

Sources & evidence

ORD record
ord-ffcfd624e7cb4d4f8af16323b486b47e
Source dataset
uspto-grants-1989_12
Patent number
US04885367

Reaction notes

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