Hydrogen Peroxide → HCID 22118448, compound

HRID 1275477Notes

Reaction equation

HRID 1275477 reaction equation
[C:1]([C:4]1[C:5]([CH3:18])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)S[CH2:9][CH2:8][CH:7]2[CH2:15][O:16][CH3:17])(=[O:3])[CH3:2].OO.[S:21](S([O-])=O)([O-:23])=[O:22].[Na+].[Na+]>C(O)(=O)C>[C:1]([C:4]1[C:5]([CH3:18])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[S:21](=[O:23])(=[O:22])[CH2:9][CH2:8][CH:7]2[CH2:15][O:16][CH3:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 24489Sodium DithioniteHCID 22118452HCID 22118452, compound

Product 1

HCID 22118448HCID 22118448, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture containing 0.30 g (1.1 mmol) of 6-acetyl-4-methoxymethyl-5,8-dimethylthiochroman, 0.39 ml of a30 wt % hydrogen peroxide aqueous solution and 0.3 ml of acetic acid was allowed to react at 60° C. for 2 hours, and further allowed to react at 80° C. for 1 hour. The reaction mixture was cooled to room temperature, and a 2 wt % sodium hydrosulfite aqueous solution was added. The mixture was extracted with ethyl acetate, and the extract was washed with a saturated sodium chloride aqueous solution. An organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off to give 0.32 g (yield 94%) of the titled compound as a crude product.

Workup

  1. customto react at 60° C. for 2 hours
  2. customto react at 80° C. for 1 hour
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with a saturated sodium chloride aqueous solution
  5. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-c5c0f98f946a41e6aaeb2e548615b9af
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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