HCID 22118403, compound → HCID 22118425, compound

HRID 1275437Notes

Reaction equation

HRID 1275437 reaction equation
Cl[O-:2].[Na+].[C:4]([C:7]1[C:8]([CH3:22])=[C:9]2[C:14](=[CH:15][CH:16]=1)[S:13](=[O:18])(=[O:17])[CH2:12][C:11]([CH3:20])([CH3:19])[C:10]2=[O:21])(=[O:6])C>O1CCOCC1.O>[C:4]([C:7]1[C:8]([CH3:22])=[C:9]2[C:14](=[CH:15][CH:16]=1)[S:13](=[O:17])(=[O:18])[CH2:12][C:11]([CH3:20])([CH3:19])[C:10]2=[O:21])([OH:6])=[O:2]

Participants

5

Reactant 2

HCID 22118403HCID 22118403, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 22118425HCID 22118425, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
28 °C

Procedure

11.6 Grams (about 9.8 mmol) of a 6.3 wt % sodium hypochlorite aqueous solution was placed in a 50-ml three-necked round-bottomed flask, and cooled to 15~20° C., and then a solution of 0.83 g (2.96 mmol) of 6-acetyl-3,3,5-trimethylthiochroman-4-one-1,1-dioxide in 5 ml of dioxane was gradually added. The mixture was stirred at 15~20° C. for 30 minutes, and then stirred at room temperature (temperature-increased to 28° C.) for 3 hours, and the reaction mixture was diluted with about 50 ml of water and washed with chloroform twice. A sodium sulfite aqueous solution was added to an aqueous layer to decompose excess hypochlorite, and then the mixture was neutralized and acidified with a 5 wt % hydrochloric acid aqueous solution to give a white solid. The solid was extracted with ethyl acetate, and an organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, to give 0.68 g (yield 81%) of 6-carboxy-3,3,5-trimethylthiochroman-4-one-1,1-dioxide in the form of a white solid.

Workup

  1. temperaturecooled to 15~20° C.
  2. stirringstirred at room temperature
  3. washwashed with chloroform twice
  4. additionA sodium sulfite aqueous solution was added to an aqueous layer
  5. customto give a white solid
  6. extractionThe solid was extracted with ethyl acetate
  7. washan organic layer was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5e5a2565f09249c9a5f05f337fbb9434
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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