3-(2-Chlorophenyl)-2-cyanopropionic acid → 3-(2-Chlorophenyl)prop-2-enenitrile

HRID 980561

Reaktionsgleichung

Reaktionsgleichung von HRID 980561
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][CH:5]([C:9]#[N:10])C(O)=O>CN(C)C=O>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH:4]=[CH:5][C:9]#[N:10]

Komponenten

3

Edukt 1

HCID 2918733-(2-Chlorophenyl)-2-cyanopropionic acid

Produkt 1

HCID 5819793-(2-Chlorophenyl)prop-2-enenitrileAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into a 1-liter, three-necked flask equipped with a mechanical stirrer, reflux condenser and nitrogen inlet is placed 138.5 g (0.66 mole) of 2-(o-chlorobenzyl)cyanoacetic acid and 220 ml of dry N,N-dimethylformamide. The mixture is stirred and slowly heated under nitrogen to reflux and held there for 6 hours. The resulting yellow mixture is allowed to cool under nitrogen overnight at room temperature. A precipitate (approximately 0.5 g) that forms is filtered off and the filtrate is poured into 1 liter of water. The organic layer is taken up in three 330-ml portions of ethyl ether/hexane (1:1 v/v), and the solutions are combined and washed once with 150 ml of water. The ethyl ether/hexane solution is dried over anhydrous magnesium sulfate, filtered and evaporated on a rotary evaporator. The residual liquid is distilled under reduced pressure through an insulated 12-inch Vigreux column with the product being collected at 82° C.-85° C./0.3 mm Hg as a colorless liquid identified by infrared, 'H and 13C nuclear magnetic resonance. The yield is 94.7 percent.

Aufarbeitung

  1. customInto a 1-liter, three-necked flask equipped with a mechanical stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. temperatureslowly heated under nitrogen
  4. temperatureto reflux
  5. filtrationA precipitate (approximately 0.5 g) that forms is filtered off
  6. additionthe filtrate is poured into 1 liter of water
  7. washwashed once with 150 ml of water
  8. dry with materialThe ethyl ether/hexane solution is dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated on a rotary evaporator
  11. distillationThe residual liquid is distilled under reduced pressure through an insulated 12-inch Vigreux column with the product
  12. custombeing collected at 82° C.-85° C./0.3 mm Hg as a colorless liquid

Quellen und Nachweise

ORD-Eintrag
ord-f0359bc0d73147c98e40aeda7f6978eb
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04638078

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