Dimethyl Sulfoxide → HCID 56622521, compound

HRID 1279582Notes

Reaction equation

HRID 1279582 reaction equation
[CH:1]([C:5]1(C(OCC)=O)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])=[CH:2][CH2:3][CH3:4].[Cl-].[Li+].CS(C)=O>O>[CH:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])=[CH:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 433294Lithium ChlorideHCID 54124948HCID 54124948, compound

Product 1

HCID 56622521HCID 56622521, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

The reagents (1-butenyl)-2-carboethoxy cyclohexanone (11.2 g, 50 mmol), lithium chloride (10.6 g, 250 mmol), water (0.99 g, 55mmol), and dimethyl sulfoxide, (250 ml) were combined under N2 and refluxed for 2 hours. The reaction was then cooled to 25° C. The reaction mixture was poured into water and extracted with two portions of 1:1 ether-hexane. The organic phases were combined and washed with two portions water followed by saturated brine and then dried over MgSO4. After filtering and stripping, the product was purified by fractional distillation at 1.5 mm Hg. (The product boils at 65 to 70° C. at 1 to 2 mm Hg.), giving 5.5 g of the desired title ketone.

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with two portions of 1:1 ether-hexane
  3. washwashed with two portions water
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtering
  6. distillationthe product was purified by fractional distillation at 1.5 mm Hg

Sources & evidence

ORD record
ord-062b962123e84b9cb4a2bb0a94477cff
Source dataset
uspto-grants-2002_09
Patent number
US06448286B1

Reaction notes

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