Acetic Acid → HCID 22118407, compound

HRID 1275440Notes

Reaction equation

HRID 1275440 reaction equation
C(O)(=O)C.OO.[Cl:7][C:8]1[CH:9]=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:11]([CH3:19])=[C:12]2[C:17]=1S[CH2:15][CH2:14][C:13]2=[O:18].[S:25]([O-:28])(O)=[O:26].[Na+]>O>[Cl:7][C:8]1[CH:9]=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:11]([CH3:19])=[C:12]2[C:17]=1[S:25](=[O:28])(=[O:26])[CH2:15][CH2:14][C:13]2=[O:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2×HCID 109021585-Methyl-6-ethoxycarbonyl-8-chlorothiochroman-4-oneHCID 23665763Sodium Bisulfite

Product 1

HCID 22118407HCID 22118407, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3 Milliliters of acetic acid and 1.75 g (15.47 mmol) of a 30 wt % hydrogen peroxide aqueous solution were added to 2.00 g (7.03 mmol) of 8-chloro-6-ethoxycarbonyl-5-methylthiochroman-4-one in a 50-ml round-bottomed flask, and the mixture was allowed to react at 70° C. for 2 hours. The reaction mixture was diluted with about 50 ml of water, and a sodium hydrogensulfite was added to decompose excess hydrogen 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. Then, the solvent was distilled off under reduced pressure to give 1.20 g (yield 54%) of 8-chloro-6-ethoxycarbonyl-5-methylthiochroman-4-one-1,1-dioxide.

Workup

  1. customto react at 70° C. for 2 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. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-34e3de4d836c4fe1a873be79114a9deb
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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