Hydrogen Peroxide → Bis[4-(2-methoxyethoxy)phenyl]sulfoxide

HRID 1753684Notes

Reaction equation

HRID 1753684 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][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][O:22][CH3:23])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.OO.O.O.O.O.O.S([O-])([O-])(=[O:33])=S.[Na+].[Na+].O>C(O)(=O)C>[CH3:23][O:22][CH2:21][CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([S:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:11][CH:10]=2)=[O:33])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 61475Sodium Thiosulfate PentahydrateHCID 117666858Bis[4-(2-methoxyethoxy)phenyl]sulfide

Product 1

HCID 117666676Bis[4-(2-methoxyethoxy)phenyl]sulfoxideYield 984.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 200 g of acetic acid was dissolved 28.5 g of bis[4-(2-methoxyethoxy)phenyl]sulfide obtained in Synthesis Example 1-33. While the solution was maintained at an internal temperature of 40° C., 7.87 g of 35 wt % aqueous hydrogen peroxide was added dropwise. The reaction solution was aged at room temperature for 15 hours, after which under ice cooling, a mixture of 2.0 g sodium thiosulfate pentahydrate and 10 g water was added dropwise to quench the reaction. The solution was concentrated in vacuum and combined with 100 g of toluene, 50 g of ethyl acetate and 50 g of water. The organic layer was separated, washed with water, and concentrated in vacuum. The concentrate was crystallized from 20 g of ethyl acetate and 300 g of hexane, obtaining 27.8 g of the target compound, bis[4-(2-methoxy-ethoxy)phenyl]sulfoxide as white crystals. Yield 91%.

Workup

  1. customobtained in Synthesis Example 1-33
  2. additionwas added dropwise
  3. additionwas added dropwise
  4. customto quench
  5. customthe reaction
  6. concentrationThe solution was concentrated in vacuum
  7. customThe organic layer was separated
  8. washwashed with water
  9. concentrationconcentrated in vacuum
  10. customThe concentrate was crystallized from 20 g of ethyl acetate and 300 g of hexane

Sources & evidence

ORD record
ord-07cc20d7358c490694c33b52862b8964
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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