Catechol → 2,3-Dihydro-1,4-benzodioxine-2-carbonitrile

HRID 394651Notes

Reaction equation

HRID 394651 reaction equation
Cl[C:2](=[CH2:5])[C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].[C:12]1([C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15])[OH:13]>CC(C)=O>[O:13]1[C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[O:15][CH2:5][CH:2]1[C:3]#[N:4]

Participants

5

Reactant 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 701982-Chloroacrylonitrile

Product 1

HCID 27358392,3-Dihydro-1,4-benzodioxine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.45 g (15.5 mmol) of 2-chloroacrylonitrile and 6 g (43.5 mmol) of dry potassium carbonate are added in succession to 6.6 g (60 mmol) of catechol dissolved in 80 ml of anhydrous acetone. The operation is repeated 4 times within one hour; the mixture is then heated to boiling. After 18 hours at reflux under argon, the reaction mixture is cooled and then filtered over Celite. After evaporation of the solvent, the residue is taken up in a water/ethyl acetate mixture (50:50) and then the aqueous phase is extracted with ethyl acetate. The organic phase, dried over magnesium sulphate and then filtered, is evaporated under reduced pressure. The title nitrile is obtained pure in the form of a white solid after purification on a silica column (eluant: AcOEt/PE 30/70).

Workup

  1. customwithin one hour
  2. temperaturethe mixture is then heated to boiling
  3. temperatureAfter 18 hours at reflux under argon
  4. temperaturethe reaction mixture is cooled
  5. filtrationfiltered over Celite
  6. customAfter evaporation of the solvent
  7. extractionthe aqueous phase is extracted with ethyl acetate
  8. dry with materialThe organic phase, dried over magnesium sulphate
  9. filtrationfiltered
  10. customis evaporated under reduced pressure

Sources & evidence

ORD record
ord-fcb922191a2545808515a643b23b5107
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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