Hydrogen Peroxide → HCID 54398044, compound

HRID 1753672Notes

Reaction equation

HRID 1753672 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:18]O.C1(C)C=CC=CC=1>C(O)(=O)C.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].O.C(OCC)(=O)C>[C:1]1([S:7]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:12][CH:13]=2)=[O:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 3

HCID 784Hydrogen PeroxideHCID 1140TolueneHCID 114138224-tert-Butyldiphenyl sulfide

Product 1

HCID 54398044HCID 54398044, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 61475Sodium Thiosulfate PentahydrateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In 160 g of acetic acid was dissolved 27.4 g of 4-tert-butylphenyl phenyl sulfide which had been synthesized according to the well-known formulation. While the solution was maintained at an internal temperature of 30° C., 9 g of 35 wt % aqueous hydrogen peroxide was added dropwise. The reaction solution was aged at room temperature for 18 hours, after which under ice cooling, a mixture of 1 g sodium thiosulfate pentahydrate and 50 g water was added dropwise to quench the reaction. The solution was combined with 200 g of toluene, 100 g of ethyl acetate, and 100 g of water. The organic layer was separated, washed with water, and concentrated in vacuum. This was followed by crystallization from hexane, filtration, and drying. There was obtained 25.4 g of the target compound, 4-tert-butylphenyl phenyl sulfoxide as white crystals. Yield 98%.

Workup

  1. customhad been synthesized
  2. additionwas added dropwise
  3. additionwas added dropwise
  4. customto quench
  5. customthe reaction
  6. customThe organic layer was separated
  7. washwashed with water
  8. concentrationconcentrated in vacuum
  9. customThis was followed by crystallization from hexane, filtration
  10. customdrying

Sources & evidence

ORD record
ord-9103958332594fb8a77b685d9f7d5b60
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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