Hydrogen Peroxide → HCID 117666755, compound

HRID 1753682Notes

Reaction equation

HRID 1753682 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[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:28])=S.[Na+].[Na+].O>C(O)(=O)C>[C:1]1([S:7]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:12][CH:13]=2)=[O:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 61475Sodium Thiosulfate PentahydrateHCID 117666794HCID 117666794, compound

Product 1

HCID 117666755HCID 117666755, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 85 g of acetic acid was dissolved 12 g of 4-(2-methoxyethoxy)phenyl phenyl sulfide obtained in Synthesis Example 1-29. While the solution was maintained at an internal temperature of 30° C., 4.5 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 1.2 g sodium thiosulfate pentahydrate and 15 g water was added dropwise to quench the reaction. The solution was combined with 80 g of methylene chloride and 40 g of water for extraction. The organic layer was separated, washed with water, and concentrated in vacuum. On subsequent crystallization from ethyl acetate/hexane, 11 g of the target compound, 4-(2-methoxyethoxy)phenyl phenyl sulfoxide was obtained as white crystals. Yield 86%.

Workup

  1. customobtained in Synthesis Example 1-29
  2. additionwas added dropwise
  3. additionwas added dropwise
  4. customto quench
  5. customthe reaction
  6. extractionThe solution was combined with 80 g of methylene chloride and 40 g of water for extraction
  7. customThe organic layer was separated
  8. washwashed with water
  9. concentrationconcentrated in vacuum
  10. customOn subsequent crystallization from ethyl acetate/hexane, 11 g of the target compound

Sources & evidence

ORD record
ord-e01733a25fa84cc68fdbea5bfac20a54
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

Loading…