Reaktion #1152431

Reaktionsgleichung

bromine

allyl cyanide

catechol

potassium carbonate

3,4-dibromobutyronitrile

→

1,4-benzodioxan-2-yl-acetonitrile

Lösungsmittel

ethyl acetate

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe starting material is prepared
2. 2
   workup.STIRRINGwhile stirring at 35° under nitrogen
3. 3
   TemperaturThe mixture is refluxed for 4 hours
4. 4
   workup.STIRRINGstirred overnight at room temperature
5. 5
   FiltrationIt is filtered
6. 6
   Waschenthe residue washed with 2,000 ml of ethyl acetate
7. 7
   Sonstigethe filtrate evaporated
8. 8
   workup.DISTILLATIONthe residue distilled
9. 9
   Sonstigethe fraction boiling at 138°/1.4-131°/1.1 mm Hg collected

Vorschrift

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.

Quelle