Catechol → 2-(2,3-Dihydro-1,4-benzodioxin-2-yl)acetonitrile

HRID 1065249Notes

Reaction equation

HRID 1065249 reaction equation
BrBr.[CH2:3]([C:6]#[N:7])[CH:4]=[CH2:5].BrC(CBr)CC#N.[C:15]1([C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[OH:18])[OH:16].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[O:16]1[C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[O:18][CH2:5][CH:4]1[CH2:3][C:6]#[N:7]

Participants

7

Reactant 5

HCID 289CatecholHCID 80093-ButenenitrileHCID 11430Potassium CarbonateHCID 24408BromineHCID 118311393,4-Dibromobutanenitrile

Product 1

HCID 2675312-(2,3-Dihydro-1,4-benzodioxin-2-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The starting material is prepared as follows: To the solution of 1,134 g of bromine in 1,400 ml of ethyl acetate 472 g of allyl cyanide are added dropwise while stirring for 90 minutes at -10°-0°. The resulting solution of 3,4-dibromobutyronitrile is added all at once to the solution prepared from 705 g of catechol and 1,987 g of anhydrous potassium carbonate in 5,000 ml of refluxing ethyl acetate, while stirring at 35° under nitrogen. The mixture is refluxed for 4 hours and stirred overnight at room temperature. It is filtered, the residue washed with 2,000 ml of ethyl acetate, the filtrate evaporated, the residue distilled and the fraction boiling at 138°/1.4-131°/1.1 mm Hg collected, to yield the 1,4-benzodioxan-2-yl-acetonitrile.

Workup

  1. customThe starting material is prepared
  2. stirringwhile stirring at 35° under nitrogen
  3. temperatureThe mixture is refluxed for 4 hours
  4. stirringstirred overnight at room temperature
  5. filtrationIt is filtered
  6. washthe residue washed with 2,000 ml of ethyl acetate
  7. customthe filtrate evaporated
  8. distillationthe residue distilled
  9. customthe fraction boiling at 138°/1.4-131°/1.1 mm Hg collected

Sources & evidence

ORD record
ord-bb7d498d071d4c2e8452b1b68b2eb9a4
Source dataset
uspto-grants-1982_05
Patent number
US04329348

Reaction notes

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