Hydrogen Peroxide → Bis(4-butoxyphenyl) sulfoxide

HRID 1753676Notes

Reaction equation

HRID 1753676 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].OO.O.O.O.O.O.S([O-])([O-])(=[O:33])=S.[Na+].[Na+].O>C(O)(=O)C>[CH2:20]([O:19][C:16]1[CH:15]=[CH:14][C:13]([S:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=2)=[O:33])=[CH:18][CH:17]=1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 61475Sodium Thiosulfate PentahydrateHCID 117666789Bis(4-butoxyphenyl) sulfide

Product 1

HCID 20458150Bis(4-butoxyphenyl) sulfoxideYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 200 g of acetic acid was dissolved 30 g of bis(4-butoxyphenyl) sulfide obtained in Synthesis Example 1-17. While the solution was maintained at an internal temperature of 30° C., 8.8 g of 35 wt % aqueous hydrogen peroxide was added dropwise. The reaction solution was aged at room temperature for 12 hours, after which under ice cooling, a mixture of 0.9 g sodium thiosulfate pentahydrate and 30 g water was added dropwise to quench the reaction. The solution was combined with 200 g of methylene chloride and 50 g of water for extraction. The organic layer was separated, washed with water, and concentrated in vacuum. On subsequent purification by silica gel chromatography, 28 g of the target compound, bis(4-butoxyphenyl) sulfoxide was obtained as amorphous solid. Yield 90%.

Workup

  1. customobtained in Synthesis Example 1-17
  2. additionwas added dropwise
  3. additionwas added dropwise
  4. customto quench
  5. customthe reaction
  6. extractionThe solution was combined with 200 g of methylene chloride and 50 g of water for extraction
  7. customThe organic layer was separated
  8. washwashed with water
  9. concentrationconcentrated in vacuum
  10. customOn subsequent purification by silica gel chromatography, 28 g of the target compound

Sources & evidence

ORD record
ord-a98881cdb0b34a8c97a415ee9a73d5d8
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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