Potassium Carbonate → HCID 69439208, compound

HRID 1350072Notes

Reaction equation

HRID 1350072 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[C:14](=O)([O:17]C)[O:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[C:10]([CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:14]([O:15][CH3:16])=[O:17])#[N:11]

Participants

7

Reactant 4

HCID 11430Potassium Carbonate2×HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 69439208HCID 69439208, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Twenty five grams of (3-methoxyphenyl)acetonitrile are dissolved in 200 ml of anhydrous THF in an Erlermeyer ground-necked flask. 60% sodium hydride (8.88 g; 0.37 mol) is added to the solution and the reaction mixture is heated at reflux for 30 minutes with stirring. Dimethyl carbonate (58 ml; 0.6814 mol) is then added dropwise in the course of half an hour and the reaction mixture is subsequently heated at reflux for 2 hours with stirring. The reaction mixture is poured into cold and slightly acidic water. The aqueous phase is extracted with ether, and then the ethereal phase is washed with water before being evaporated. A solution of potassium carbonate (47.15 g; 0.34 mol ) is added to the oil obtained above. After stirring, the mixture is washed with ether. The ethereal phase obtained is rewashed with a solution of potassium carbonate (12.02 g; 0.08 mol). The two aqueous phases are combined, immediately acidified, and extracted with ether. The organic phase so obtained is washed with a 10% sodium hydrogen carbonate solution, dried over magnesium sulphate and evaporated under reduced pressure to yield the title product in the form of an orangey yellow oil.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 30 minutes
  3. temperaturethe reaction mixture is subsequently heated
  4. temperatureat reflux for 2 hours
  5. stirringwith stirring
  6. extractionThe aqueous phase is extracted with ether
  7. washthe ethereal phase is washed with water
  8. custombefore being evaporated
  9. customobtained above
  10. stirringAfter stirring
  11. washthe mixture is washed with ether
  12. customThe ethereal phase obtained
  13. extractionextracted with ether
  14. customThe organic phase so obtained
  15. washis washed with a 10% sodium hydrogen carbonate solution
  16. dry with materialdried over magnesium sulphate
  17. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-41186302b0914158a82bdadf90f8010b
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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