Acetone → Diallyl sulfone

HRID 564339Notes

Reaction equation

HRID 564339 reaction equation
[CH2:1](O)[CH:2]=[CH2:3].O[O:6][S:7]([O-:9])=O.[K+].[CH3:11][C:12]([CH3:14])=O>O>[CH2:1]([S:7]([CH2:14][CH:12]=[CH2:11])(=[O:9])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 180AcetoneHCID 7858Allyl AlcoholHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 159797Diallyl sulfoneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of allyl alcohol isomer A from Step 2 (7.11 g, 16.65 mmol) and oxone (30.75 g, 50.0 mmol) in acetone (100 mL) and water (25 mL) was stirred at RT overnight then filtered, diluted with water and AcOEt, extracted with AcOEt, dried and concentrated. The residue is purified was purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 99:1 to 60:40) to provide 5.50 g (72%) of allylsulfone.

Workup

  1. filtrationthen filtered
  2. additiondiluted with water and AcOEt
  3. extractionextracted with AcOEt
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified
  7. customwas purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 99:1 to 60:40)

Sources & evidence

ORD record
ord-d6e63dc26e2248b4b93a5bb95fa6cb07
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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