Water → 7-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one

HRID 339175Notes

Reaction equation

HRID 339175 reaction equation
[C:1]1([S:7][C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][CH2:14][C:15]3=[O:18])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:19]OS([O-])=O.[K+].[OH2:25]>CO>[C:1]1([S:7]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][CH2:14][C:15]3=[O:18])=[CH:10][CH:9]=2)(=[O:19])=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 590217307-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 590217777-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-oneYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one ( ) was dissolved in 50 mL of MeOH and stirred at room temperature. OXONE™ (13.5 g, 22 mmol) was dissolved in 10 mL of water and added to the stirring reaction. The reaction mixture was stirred for 8 hours, and then evaporated under reduced pressure. The resulting aqueous residue was diluted with 200 mL of water and extracted three times with 100 mL of EtOAc. The combined extracts were dried over MgSO4, and the solvent was removed under reduced pressure to yield an oil which was eluted through silica gel with 1:1 EtOAc/hexanes. Removal of solvent under reduced pressure afforded 1.7 g (5.9 mmol, 59%) of 7-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one as an oil. MS: 287 (M+H)+.

Workup

  1. additionadded to the stirring reaction
  2. stirringThe reaction mixture was stirred for 8 hours
  3. customevaporated under reduced pressure
  4. additionThe resulting aqueous residue was diluted with 200 mL of water
  5. extractionextracted three times with 100 mL of EtOAc
  6. dry with materialThe combined extracts were dried over MgSO4
  7. customthe solvent was removed under reduced pressure
  8. customto yield an oil which
  9. washwas eluted through silica gel with 1:1 EtOAc/hexanes
  10. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-ac1bf5e6533a441a825fab359f006b31
Source dataset
uspto-grants-2014_11
Patent number
US08889906B2

Reaction notes

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