Potassium Iodide → HCID 54039813, compound

HRID 1613559Notes

Reaction equation

HRID 1613559 reaction equation
C1(S[CH2:8][C:9]2([C:12]([OH:15])([CH3:14])[CH3:13])[CH2:11][CH2:10]2)C=CC=CC=1.C(=O)(O)[O-].[Na+].Cl[C:22]1[CH:27]=[CH:26][CH:25]=[C:24](C(OO)=O)[CH:23]=1.[S:32]([O-:36])([O-])(=[O:34])=S.[Na+].[Na+].[I-].[K+]>ClCCl.O>[C:22]1([S:32]([CH2:8][C:9]2([C:12]([OH:15])([CH3:14])[CH3:13])[CH2:11][CH2:10]2)(=[O:36])=[O:34])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 54145545HCID 54145545, compound

Product 1

HCID 54039813HCID 54039813, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7 (4.83 g, 21.3 mmol) in dichloromethane (50 mL) was added sodium bicarbonate (10.1 g, 120 mmol) and water (65 mL) and the mixture was stirred vigorously in an ice bath. To the mixture was added m-chloroperbenzoic acid (ca. 85%, 10.4 g, 51.2 mmol) portionwise and the mixture was stirred for 20 min. The excess amount of peracid was decomposed with sodium thiosulfate solution in the presence of potassium iodide. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, and dried over sodium sulfate. Filtration and concentration gave 6.30 g of an oily material, which was purified by column chromatography (silica gel 50 g, 5-33% ethyl acetate in n-hexane) to give 4.05 g (74.8%) of 8, as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 20 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-8b3e0eb494ca48f1ae93fdfa64e8a255
Source dataset
uspto-grants-1993_03
Patent number
US05194431

Reaction notes

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