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Hydrogen Peroxide → 5-Tert-butyl-1-methanesulphinyl-2-methoxy-3-nitro-benzene

HRID 2360510
Notes
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Reaction equation

HRID 2360510 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([S:11][CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH:18]O>C(O)(C(F)(F)F)C(F)(F)F.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([S:11]([CH3:12])=[O:18])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 584939295-Tert-butyl-2-methoxy-1-methylsulphanyl-3-nitro-benzene

Product 1

HCID 584939515-Tert-butyl-1-methanesulphinyl-2-methoxy-3-nitro-benzene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent
HCID 24477
Sodium Thiosulfate
Solvent

Procedure

0.5 g of 5-tert-butyl-2-methoxy-1-methylsulphanyl-3-nitro-benzene are dissolved in 15 ml of 1,1,1,3,3,3-hexafluoroisopropanol, combined with 1.1 ml of a 9 M solution of hydrogen peroxide in water and stirred for 5 hours at ambient temperature. Then the mixture is cooled to 0° C. and diluted with 10% aqueous sodium thiosulphate solution. The mixture is extracted 3 times with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution. After drying with sodium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (petroleum ether/ethyl acetate 95:5).

Workup

  1. temperatureThen the mixture is cooled to 0° C.
  2. extractionThe mixture is extracted 3 times with ethyl acetate
  3. washthe combined organic phases are washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialAfter drying with sodium sulphate the solvents
  5. customthe residue is chromatographed on silica gel (petroleum ether/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-8b70f58496c54ef693dc81b511e552d2
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08686022B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes