Hydrogen Peroxide → 1,4-Dioxa-8lambda4-thiaspiro(4.5)decan-8-one

HRID 1600158Notes

Reaction equation

HRID 1600158 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][S:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[OH:11]O>C(O)(=O)C>[O:4]1[C:5]2([CH2:10][CH2:9][S:8](=[O:11])[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 123359781,4-Dioxa-8-thiaspiro(4.5)decane

Product 1

HCID 132737821,4-Dioxa-8lambda4-thiaspiro(4.5)decan-8-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A room temperature mixture of 13.8 g of product from Example 392 dissolved in 100 ml of acetic acid is treated, dropwise over 20 minutes, with 9.0 mlof 30% hydrogen peroxide. The reaction mixture is stirred at room temperature for 1 hour, concentrated in vacuo at 50° C., and extracted with ethyl acetate. The organic layer is washed 2 X with saturated sodium bicarbonate, water and saturated sodium chloride, dried and concentrated in vacuo. The aqueous washes are combined and concentrated in vacuo to about 25 ml. The residue is saturated with solid potassium carbonate and extracted 2 X with 200 ml of ethyl acetate. The organic phase is concentrated in vacuo to a solid which is triturated withhexane and collected to give 13.1 g of the desired product.

Workup

  1. concentrationconcentrated in vacuo at 50° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed 2 X with saturated sodium bicarbonate, water and saturated sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo
  6. concentrationconcentrated in vacuo to about 25 ml
  7. extractionextracted 2 X with 200 ml of ethyl acetate
  8. concentrationThe organic phase is concentrated in vacuo to a solid which
  9. customis triturated withhexane
  10. customcollected

Sources & evidence

ORD record
ord-a6eb9fc87327481fb9d320cdef9d3022
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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