Acetone → HCID 11140821, compound

HRID 1872866Notes

Reaction equation

HRID 1872866 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6](=[O:17])(=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C(=O)([O-])[O-].[K+].[K+].I[CH:25]([CH3:27])[CH3:26].CC(C)=O>CCCCCC>[CH:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6](=[O:17])(=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3)([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 18687760HCID 18687760, compound

Product 1

HCID 11140821HCID 11140821, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 1.00 gm (0.0043 mole) of 3-hydroxyphenoxathiin 10,10-dioxide (Example 7) 1.48 gm (0.0107 mole) of anhydrous granular potassium carbonate, 5.5 mL of 2-iodopropane (Aldrich Chemical Co.), and 60 mL of acetone were stirred overnight. The acetone was removed under water pump vacuum and the residue mixed with methylene chloride and filtered. The filtrate was washed with 2×200 mL of water and dried over magnesium sulfate. The solvent was removed under water pump vacuum to give an oil. Some hexane was added to the oil and the mixture heated on a steam bath. This gave a white solid which was recrystallized from ethyl acetate/hexane to yield 0.75 gm of 3-isopropoxyphenoxathiin 10,10-dioxide, m.p. 94-95°.

Workup

  1. customThe acetone was removed under water pump vacuum
  2. additionthe residue mixed with methylene chloride
  3. filtrationfiltered
  4. washThe filtrate was washed with 2×200 mL of water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under water
  7. customto give an oil
  8. temperaturethe mixture heated on a steam bath
  9. customThis gave a white solid which
  10. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-bab0fc8156914af1b08c94413f362beb
Source dataset
uspto-grants-2000_08
Patent number
US06110961

Reaction notes

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