Hydrogen Peroxide → HCID 117666905, compound

HRID 1753680Notes

Reaction equation

HRID 1753680 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:20]O.C1(C)C=CC=CC=1>C(O)(=O)C.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].O.C(OCC)(=O)C>[C:1]1([S:7]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:13]=2)=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 784Hydrogen PeroxideHCID 1140TolueneHCID 117666944HCID 117666944, compound

Product 1

HCID 117666905HCID 117666905, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 61475Sodium Thiosulfate PentahydrateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In 100 g of acetic acid was dissolved 13.8 g of 4-cyclopentyloxyphenyl phenyl sulfide obtained in Synthesis Example 1-25. While the solution was maintained at an internal temperature of 30° C., 4.8 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 0.5 g sodium thiosulfate pentahydrate and 15 g water was added dropwise to quench the reaction. The solution was 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. This was followed by crystallization from hexane, filtration and drying, obtaining 13.5 g of the target compound, 4-cyclopentyloxyphenyl phenyl sulfoxide as white crystals. Yield 96%.

Workup

  1. customobtained in Synthesis Example 1-25
  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
  9. customThis was followed by crystallization from hexane, filtration
  10. customdrying

Sources & evidence

ORD record
ord-ab6ff65f637640fd9be3d9320935f8bc
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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