Water → 6-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one

HRID 2103335Notes

Reaction equation

HRID 2103335 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12][CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:19]OS([O-])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[OH2:33]>CO.CC#N>[C:1]1([S:7]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12][CH2:11]3)(=[O:19])=[O:33])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10313463Potassium peroxymonosulphateHCID 149576696-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-oneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 590217396-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-oneYield 72.27%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

A solution of 6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one (8.05 g, 31.65 mmol) in MeOH/MeCN (50 mL of each) was stirred at room temperature. OXONE™ (potassium peroxymonosulfate, 77.83 g, 126.60 mmol) was dissolved in 50 mL of water and was added to the stirring reaction. The reaction mixture was stirred for 15 hours, and then evaporated under reduced pressure. The resulting aqueous residue was diluted with 500 mL of water and extracted three times with 300 mL of EtOAc. The combined extracts were washed with water, saturated brine, and dried over MgSO4. The solvent was removed under reduced pressure to yield an oil which was eluted through silica gel with hexane followed by chloroform. Removal of solvent under reduced pressure afforded 6.55 g (22.87 mmol, 72.27%) of 6-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one as a white solid, which was recrystallized from EtO2/hexanes. MS: 287 (M+H)+.

Workup

  1. additionwas added to the stirring reaction
  2. customevaporated under reduced pressure
  3. additionThe resulting aqueous residue was diluted with 500 mL of water
  4. extractionextracted three times with 300 mL of EtOAc
  5. washThe combined extracts were washed with water, saturated brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customto yield an oil which
  9. washwas eluted through silica gel with hexane
  10. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-3324fe1797214da4b25b9a776f4cfb54
Source dataset
uspto-grants-2009_08
Patent number
US07576103B2

Reaction notes

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