Methanol → HCID 22316712, compound

HRID 1691840Notes

Reaction equation

HRID 1691840 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1SC.O[O:15][S:16]([O-:18])=O.[K+].[CH3:20]O>C(#N)C.O>[CH3:20][S:16]([C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[O:2][CH3:1])(=[O:18])=[O:15]

Participants

6

Reactant 3

HCID 887MethanolHCID 6079362-Methylthio-5-nitro anisoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22316712HCID 22316712, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

2-Methoxy-1-methylsulfanyl-4-nitro-benzene (797 mg, 4.0 mmol) was dissolved in methanol (10 ml) and acetonitrile (10 ml). A solution of Oxone (1.5 eq, 3.7 g) in 8 ml of water was added and the mixture was allowed to stir at room temperature for 4 hours. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1-methanesulfonyl-2-methoxy-4-nitro-benzene (631 mg, 68.2%) as a yellow crystalline solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b04883d281604a12bf60a179c66a92ea
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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