1,2-Dichloroethane → 1-(4-Ethoxyphenyl)cyclopropanecarbonitrile

HRID 867912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 867912
[CH2:1]([Li])[CH2:2]CC.[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=1)[CH3:7].ClCCCl.Cl>CCCCCC.O1CCCC1.CCOCC>[C:16]([C:15]1([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:6][CH3:7])=[CH:10][CH:11]=2)[CH2:2][CH2:1]1)#[N:17]

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 5839052-(4-Ethoxyphenyl)acetonitrileHCID 178418339Butyllithium

Produkt 1

HCID 135372511-(4-Ethoxyphenyl)cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To 7.5 ml (0.012 mol) of 1.7M n-butyllithium in hexane, at room temperature, under an atmosphere of nitrogen, is added rapidly 10 ml of anhydrous tetrahydrofuran, followed by a solution of 4-ethoxyphenyl acetonitrile (0.8 g 0.005 mol) in 4 ml of tetrahydrofuran, during 5 minutes. The reaction mixture is stirred magnetically for 1 hour then treated with 0.50 g (0.005 mol) of 1,2-dichloroethane in 10 ml of tetrahydrofuran, during a period of 40 minutes (slow addition is important). After 16 hours, the mixture is hydrolysed by 10 ml of 3N HCl and then taken up in ether, washed with water, sodium bicarbonate, water and dried over anhydrous sodium sulphate. The solvent is removed under reduced pressure. Yield: 0.64 g of a viscous semi-crystalline oil.

Aufarbeitung

  1. addition(slow addition is important)
  2. waitAfter 16 hours
  3. washwashed with water, sodium bicarbonate, water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-59ac74d9863d4a3695aa328bbcd68d0d
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04777185

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