Acetone → Diallyl sulfone

HRID 1047508Notes

Reaction equation

HRID 1047508 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-59046acae8df4ad0ba5efa000f86c0cf
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

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