Hydrochloric Acid → 2-(4-Ethenylphenyl)ethane-1,1,2-tricarbonitrile

To a mixture of 2.00 g 4-(2,2′-dicyanoethenyl)styrene (11 mmol) and 30 mL ethanol was added a solution of 1.45 g potassium cyanide (22 mmol) in 3 mL water. The mixture was stirred at room temperature for 17 hours. 1.8 mL concentrated HCl (22 mmol) was then added and the mixture was concentrated under vacuum. Ten milliliters (10 mL) water was added to the residue, and the mixture was extracted with ethyl acetate. The combined organic layers were concentrated under vacuum, and the product was purified by column chromatography on silica gel using 20% ethyl acetate in hexane. The product recovered from the separation was mixed with 1.5 mL methylene chloride and 10 mL hexane, then filtered. A white solid was obtained (1.009 g, 44%).

1. concentrationthe mixture was concentrated under vacuum
2. additionTen milliliters (10 mL) water was added to the residue
3. extractionthe mixture was extracted with ethyl acetate
4. concentrationThe combined organic layers were concentrated under vacuum
5. customthe product was purified by column chromatography on silica gel using 20% ethyl acetate in hexane
6. customThe product recovered from the separation
7. additionwas mixed with 1.5 mL methylene chloride and 10 mL hexane
8. filtrationfiltered
9. customA white solid was obtained (1.009 g, 44%)

ORD record

ord-d0e80cce52904ae99f0b8ca78cfa11f8

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279777B2