Acetic Acid → HCID 22118408, compound

HRID 1275433Notes

Reaction equation

HRID 1275433 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][C:8]([CH3:16])([CH3:15])[C:7]2=[O:17])(=[O:3])[CH3:2].C(O)(=O)C.OO.[S:25]([O-:28])(O)=[O:26].[Na+]>O>[C:1]([C:4]1[C:5]([CH3:18])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[S:25](=[O:28])(=[O:26])[CH2:16][C:8]([CH3:15])([CH3:9])[C:7]2=[O:17])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 22118438HCID 22118438, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 22118408HCID 22118408, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100-ml round-bottomed flask was charged with 1.18 g (4.50 mmol) of 6-acetyl-3,3,5,8-tetramethylthiochroman-4-one, 2 ml of acetic acid and 1.12 g (9.88 mmol) of a 30 wt % hydrogen peroxide aqueous solution, and the mixture was allowed to react at 80° C. for 2 and half hours. The reaction mixture was diluted with about 30 ml of water, and a sodium hydrogensulfite aqueous solution was added to decompose excess peroxide. Then, the 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 1.28 g (yield 97%) of 6-acetyl-3,3,5,8-tetramethylthiochroman-4-one-1,1-dioxide.

Workup

  1. customto react at 80° C. for 2 and half hours
  2. extractionThen, the mixture was extracted with ethyl acetate
  3. washAn organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6fbfa37d1e194014900a6a29686abb86
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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