Hydrogen Peroxide → HCID 117666424, compound

HRID 1753686Notes

Reaction equation

HRID 1753686 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OO.O.O.O.O.O.S([O-])([O-])(=[O:31])=S.[Na+].[Na+]>C(O)(=O)C.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:1]1([S:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:10][CH:9]=2)=[O:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 784Hydrogen PeroxideHCID 61475Sodium Thiosulfate PentahydrateHCID 117666874HCID 117666874, compound

Product 1

HCID 117666424HCID 117666424, compoundYield 993.8%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 770 g of acetic acid was dissolved 109.3 g of 4-[2-(2-methoxyethoxy)ethoxy]phenyl phenyl sulfide obtained in Synthesis Example 1-38. While the solution was maintained at an internal temperature of 30° C., 34.5 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 8.8 g sodium thiosulfate pentahydrate and 80 g water was added dropwise to quench the reaction. The solution was combined with 200 g of toluene, 200 g of ethyl acetate and 200 g of water. The organic layer was separated, washed with water, and concentrated in vacuum, obtaining 112.9 g of the target compound, 4-[2-(2-methoxyethoxy)ethoxy]phenyl phenyl sulfoxide as oily matter. Yield 92%.

Workup

  1. customobtained in Synthesis Example 1-38
  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-0e943e5184434a49bdb93f4f9e2c88fb
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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