Hydrochloric Acid → 1-(4-Ethoxyphenyl)cyclopropanecarbonitrile

HRID 986406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986406
[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].ClC(Cl)C.Cl>C1COCC1>[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

6

Edukt 4

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 5839052-(4-Ethoxyphenyl)acetonitrileHCID 178418339Butyllithium

Produkt 1

HCID 135372511-(4-Ethoxyphenyl)cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

1.6M n-Butyllithium (680 ml) is added over 5 min to a stirred solution of 4-ethoxyphenyl acetonitrile (56 g) in anhydrous THF (600 ml) at 25° C. under an atmosphere of nitrogen. After 1 h, a solution of 1.2 dichloroethane (111 g) in anhydrous THF (300 ml) is added dropwise over 2 h and the mixture stirred at 25° C. for 16 h. The mixture is then poured onto 3N HCl (1 l ), concentrated under reduced pressure, extracted with diethyl ether (x3), washed with water, dried over anhydrous sodium sulphate, the solvent removed under reduced pressure and the residue distilled to give the product, b.p. 116°-120° C., yield 40 g. nD 1.5320.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with diethyl ether (x3)
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe solvent removed under reduced pressure
  6. distillationthe residue distilled
  7. customto give the product, b.p. 116°-120° C., yield 40 g

Quellen und Nachweise

ORD-Eintrag
ord-a27941921a974a759477b10eaf5cb161
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04713392

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