Acetic Acid → HCID 22118379, compound

HRID 1275436Notes

Reaction equation

HRID 1275436 reaction equation
C(O)(=O)C.OO.[C:7]([C:10]1[C:11]([CH3:24])=[C:12]2[C:17](=[C:18]([Cl:20])[CH:19]=1)S[CH2:15][C:14]([CH3:22])([CH3:21])[C:13]2=[O:23])(=[O:9])[CH3:8].[S:25]([O-:28])(O)=[O:26].[Na+]>O>[C:7]([C:10]1[C:11]([CH3:24])=[C:12]2[C:17](=[C:18]([Cl:20])[CH:19]=1)[S:25](=[O:28])(=[O:26])[CH2:22][C:14]([CH3:21])([CH3:15])[C:13]2=[O:23])(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2×HCID 22118433HCID 22118433, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 22118379HCID 22118379, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 Milliliters of acetic acid and 2.12 g (18.71 mmol) of a 30 wt % hydrogen peroxide aqueous solution were added to 2.20 g (7.79 mmol) of 6-acetyl-8-chloro-3,3,5-trimethylthiochroman-4-one in a 100-ml round-bottomed flask, and the mixture was reached at 80° C. for 2.5 hours. The reaction mixture was diluted with about 50 ml of water, and a sodium hydrogensulfite aqueous solution was added to decompose excess hydrogen peroxide. Then, the reaction mixture was extracted with ethyl acetate. An organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 2.16 g (yield 88%) of 6-acetyl-8-chloro-3,3,5-trimethylthiochroman-4-one-1,1-dioxide.

Workup

  1. extractionThen, the reaction mixture was extracted with ethyl acetate
  2. washAn organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-da36201c592a4b8a8d50fed1d11f0a87
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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