Sodium hydride → alpha-(4-Tert-butylphenyl)-beta-hydroxy-beta-(2-trifluoromethylphenyl)acrylonitrile

HRID 1168413

Reaktionsgleichung

Reaktionsgleichung von HRID 1168413
[H-].[Na+].[C:3]([C:7]1[CH:15]=[CH:14][C:10]([CH2:11][C:12]#[N:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>O1CCCC1>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([C:11](=[C:20]([OH:21])[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[C:17]([F:16])([F:27])[F:28])[C:12]#[N:13])=[CH:14][CH:15]=1)([CH3:6])([CH3:4])[CH3:5]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 76784(4-tert-Butylphenyl)acetonitrile

Produkt 1

HCID 70026415alpha-(4-Tert-butylphenyl)-beta-hydroxy-beta-(2-trifluoromethylphenyl)acrylonitrileAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture comprising 5.8 g of 63% sodium hydride and 137 ml of tetrahydrofuran was heated, and a mixture comprising 13.5 g of 4-tert-butylbenzyl cyanide, 15.0 g of 2-trifluoromethylbenzoyl chloride and 50 ml of tetrahydrofuran, was dropwise added thereto over a period of 2 hours under reflux. After completion of the dropwise addition, the reaction was carried out at the same temperature for 2 hours. Tetrahydrofuran in the reaction mixture was distilled off, and 250 ml of water was poured into the residue. Then, 80 ml of n-hexane was added thereto, and the mixture was stirred and washed for 10 minutes and then left to stand for 30 minutes. Then, the aqueous layer was separated. To the aqueous layer, 8.3 g of concentrated hydrochloric acid was gradually dropwise added with stirring, followed by further stirring for 30 minutes. Precipitated crystals were collected by filtration and washed with 100 ml of water and then dried at 55° C. for 24 hours to obtain 23.7 g of the desired product. The NMR spectrum data of this product were as follows.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureover a period of 2 hours under reflux
  3. additionAfter completion of the dropwise addition
  4. distillationTetrahydrofuran in the reaction mixture was distilled off
  5. addition250 ml of water was poured into the residue
  6. additionThen, 80 ml of n-hexane was added
  7. washwashed for 10 minutes
  8. waitleft
  9. waitto stand for 30 minutes
  10. customThen, the aqueous layer was separated
  11. additionTo the aqueous layer, 8.3 g of concentrated hydrochloric acid was gradually dropwise added
  12. stirringwith stirring
  13. stirringby further stirring for 30 minutes
  14. customPrecipitated crystals
  15. filtrationwere collected by filtration
  16. washwashed with 100 ml of water
  17. customdried at 55° C. for 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-64516fe875a94d00b4e64e4a1acf5ddd
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06624179B1

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