Dimethyl Sulfoxide → 6007-96-1

HRID 1925631Notes

Reaction equation

HRID 1925631 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:11])[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1.[CH3:12]S(C)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:3][C:4]1([CH3:11])[CH2:9][CH2:8][C:7](=[CH2:12])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 138166Cyclohexanone, 4,4-dimethyl-

Product 1

HCID 5729646007-96-1

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

Methyltriphenylphosphonium bromide (2.97 g, 8.3 mmol) was added in the dehydrated DMSO (8 mL) solution of sodium hydride (0.35 g, 8.7 mmol) in an ice bath. The reaction mixture was stirred at room temperature for 10 minutes, and the dehydrated DMSO solution (1.5 mL) of 4,4-dimethyl-cyclohexanone (1.0 g, 7.9 mmol) was added slowly in an ice bath. The reaction mixture was stirred at room temperature for 18 hours and poured into ice water. The organic layer was extracted with diethyl ether, and then the layer was washed with water and dried with anhydrous magnesium sulfate, and removed by filtration. The filtrate was concentrated until becoming about half in volume. The formed insoluble matter was removed by filtration, then the filtrate was removed by distillation under reduced pressure, and colorless oily matter (0.91 g) was obtained.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. extractionThe organic layer was extracted with diethyl ether
  3. washthe layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customremoved by filtration
  6. concentrationThe filtrate was concentrated
  7. customThe formed insoluble matter was removed by filtration
  8. customthe filtrate was removed by distillation under reduced pressure
  9. customcolorless oily matter (0.91 g) was obtained

Sources & evidence

ORD record
ord-33d01ce969c64bb6ae3cee68e232491a
Source dataset
uspto-grants-2012_05
Patent number
US08178681B2

Reaction notes

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