Hydrogen Peroxide → HCID 67608820, compound

HRID 1753687Notes

Reaction equation

HRID 1753687 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.[OH:30]O.O.C1(C)C=CC=CC=1>C(O)(=O)C.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH3:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([S:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:10][CH:11]=2)=[O:30])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962Water2×HCID 1140TolueneHCID 117666484HCID 117666484, compound

Product 1

HCID 67608820HCID 67608820, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 61475Sodium Thiosulfate PentahydrateCatalystHCID 176Acetic AcidSolvent

Procedure

In 200 g of acetic acid was dissolved 26.6 g of bis[4-[2-(2-methoxyethoxy)ethoxy]phenyl]sulfide obtained in Synthesis Example 1-42. While the solution was maintained at an internal temperature of 30° C., 6.4 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 0.5 g sodium thiosulfate pentahydrate and 20 g water was added dropwise to quench the reaction. The solution was combined with 200 g of toluene and 100 g of water. The organic layer was separated, washed with water, and concentrated in vacuum, obtaining 26.1 g of the target compound, bis[4-[2-(2-methoxyethoxy)ethoxy]phenyl]sulfoxide as oily matter. Yield 95%.

Workup

  1. customobtained in Synthesis Example 1-42
  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

Sources & evidence

ORD record
ord-d2c567538e5d49c0a468d782383acc0f
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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