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

HRID 2242601Notes

Reaction equation

HRID 2242601 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-e81bdc45a14d46979a28c72383ab638c
Source dataset
uspto-grants-2010_03
Patent number
US07671235B2

Reaction notes

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