HCID 22118408, compound → HCID 15477826, compound

HRID 1275434Notes

Reaction equation

HRID 1275434 reaction equation
Cl[O-:2].[Na+].[C:4]([C:7]1[C:8]([CH3:23])=[C:9]2[C:14](=[C:15]([CH3:17])[CH:16]=1)[S:13](=[O:19])(=[O:18])[CH2:12][C:11]([CH3:21])([CH3:20])[C:10]2=[O:22])(=[O:6])C>O1CCOCC1.O>[C:4]([C:7]1[C:8]([CH3:23])=[C:9]2[C:14](=[C:15]([CH3:17])[CH:16]=1)[S:13](=[O:19])(=[O:18])[CH2:12][C:11]([CH3:20])([CH3:21])[C:10]2=[O:22])([OH:6])=[O:2]

Participants

5

Reactant 2

HCID 22118408HCID 22118408, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 15477826HCID 15477826, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
30 °C

Procedure

17.8 Grams (about 15 mmol) of a 6.4 wt % sodium hypochlorite aqueous solution was placed in a 100-ml three-necked round-bottomed flask, and cooled to 15~20° C., and then a solution of 1.26 g (4.26 mmol) of 6-acetyl-3,3,5,8-tetramethylthiochroman-4-one-1,1-dioxide in 8 ml of dioxane was gradually added. The mixture was stirred at 15~20° C. with external cooling for 30 minutes, and then stirred at room temperature (temperature-increased to about 30° C.) for 3 hours. The reaction mixture was diluted with about 50 ml of water and washed with chloroform twice. A sodium sulfate aqueous solution was added to an aqueous layer to decompose excess hypochlorite, and then the aqueous solution 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 diluted hydrochloric acid and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 1.06 g (yield 84%) of 6-carboxy-3,3,5,8-tetramethylthiochroman-4-one-1,1-dioxide in the form of a white solid.

Workup

  1. temperaturecooled to 15~20° C.
  2. temperaturewith external cooling for 30 minutes
  3. stirringstirred at room temperature
  4. washwashed with chloroform twice
  5. additionA sodium sulfate aqueous solution was added to an aqueous layer
  6. customto give a white solid
  7. extractionThe solid was extracted with ethyl acetate
  8. washan organic layer was washed with diluted hydrochloric acid and with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d71e9469b53946768be023db860a2f55
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

Loading…