Hydrogen Peroxide → HCID 23450721, compound

HRID 1839883Notes

Reaction equation

HRID 1839883 reaction equation
[C:1]([C:4]1[C:5]([CH3:17])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)S[CH2:9][CH2:8][CH:7]2[CH2:15][CH3:16])(=[O:3])[CH3:2].OO.[S:20]([O-:23])(O)=[O:21].[Na+]>C(O)(=O)C>[C:1]([C:4]1[C:5]([CH3:17])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[S:20](=[O:23])(=[O:21])[CH2:9][CH2:8][CH:7]2[CH2:15][CH3:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 23450683HCID 23450683, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 23450721HCID 23450721, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixed solution containing 1.66 g (6.68 mmol) of the 6-acetyl-4-ethyl-5,8-dimethylthiochroman, 2.28 g (20.1 mmol) of a 30% hydrogen peroxide aqueous solution and 2.0 ml of acetic acid was allowed to react at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, a 2% sodium hydrogensulfite aqueous solution was added, and the mixture was extracted with ethyl acetate and washed with a saturated sodium hydrogencarbonate and then with a saturated sodium chloride aqueous solution. An organic layer was dried over anhydrous sodium sulfate and filtered, and then the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (silica gel; hexane/ethyl acetate=2:1) to give 1.03 g (yield 55%) of 6-acetyl-4-ethyl-5,8-dimethylthiochroman-1,1-dioxide.

Workup

  1. customto react at 80° C. for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with a saturated sodium hydrogencarbonate
  4. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel; hexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b63b71b765fd480aafba33ed5ef5e0fa
Source dataset
uspto-grants-2004_01
Patent number
US06677460B1

Reaction notes

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