Dimethyl Sulfate → HCID 54443769, compound

HRID 2372916Notes

Reaction equation

HRID 2372916 reaction equation
O[C:2]1[C:7](=[O:8])[C:6]([CH3:10])([CH3:9])[C:5](=[O:11])[C:4](=[CH:12][CH:13]=[C:14]2[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[C:17](=[O:23])[C:16]([OH:24])=[CH:15]2)[CH:3]=1.S([O:30][CH3:31])(OC)(=O)=O.[C:32](=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(#N)C>[CH3:32][O:24][C:16]1[C:17](=[O:23])[C:18]([CH3:22])([CH3:21])[C:19](=[O:20])[C:14](=[CH:13][CH:12]=[C:4]2[C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[C:7](=[O:8])[C:2]([O:30][CH3:31])=[CH:3]2)[CH:15]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 86745602HCID 86745602, compound

Product 1

HCID 54443769HCID 54443769, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

4 g of bis(3-hydroxy-5,5-dimethyl-4,6-dioxocyclohex-2-enylidene)ethane (from Example 3) were dissolved in a mixture of 240 ml of dioxane and 240 ml of acetonitrile by refluxing under nitrogen. 16 g of dimethyl sulfate were then added, followed by 12 g of finely crushed anhydrous potassium carbonate. The batch turned greenish blue at once, but became yellow in the course of an hour of heating under reflux. The reaction mixture was filtered while still hot, the filter cake was washed with acetonitrile, and the combined organic phases were concentrated in a rotary evaporator. The residues of alkylating agent were removed by digestion with ether, and the insolubles were removed by heating in chloroform. The filtrate was concentrated and the residue was repeatedly recrystallized from acetone. This gave a solid in the form of reddish yellow prisms.

Workup

  1. temperatureby refluxing under nitrogen
  2. custombecame yellow in the course of an hour
  3. temperatureof heating
  4. temperatureunder reflux
  5. filtrationThe reaction mixture was filtered while still hot, the filter cake
  6. washwas washed with acetonitrile
  7. concentrationthe combined organic phases were concentrated in a rotary evaporator
  8. customwere removed by digestion with ether
  9. customthe insolubles were removed
  10. temperatureby heating in chloroform
  11. concentrationThe filtrate was concentrated
  12. customthe residue was repeatedly recrystallized from acetone
  13. customThis gave a solid in the form of reddish yellow prisms

Sources & evidence

ORD record
ord-5ac542e07ed848f4a5722ecc515c6925
Source dataset
uspto-grants-1992_03
Patent number
US05101032

Reaction notes

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