Water → (6-Hydroxy-2-naphthyl)-propanonitrile

HRID 485980

Reaktionsgleichung

Reaktionsgleichung von HRID 485980
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]([CH3:20])[C:18]#[N:19])[CH:11]=[CH:10]2.O>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]([CH3:20])[C:18]#[N:19])[CH:11]=[CH:10]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 6073442-(6-Methoxynaphthalen-2-yl)propanenitrile

Produkt 1

HCID 19097091(6-Hydroxy-2-naphthyl)-propanonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

15.6 g of boron tribromide, were dissolved in 100 ml of methylene chloride and cooled to -10° C. To this, 80 ml of methylene chloride solution of 6.0 g oa (6-methoxy-2-naphthyl)-propanonitrile were added dropwise over 2 hours, followed by stirring for 7 hours at room temperature. The resulting reaction mixture was poured into 500 ml of iced water and extracted with ether, followed by washing the ether phase twice with water and then distilling off the solvent. The resulting solid was recrystallized with chloroform-hexane mixture to obtain 4.5 g of oa (6-hydroxy-2-naphthyl)-propanonitrile.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionextracted with ether
  3. washby washing the ether phase twice with water
  4. distillationdistilling off the solvent
  5. customThe resulting solid was recrystallized with chloroform-hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-81b07f2ae90c49bd8a01d86d2b012271
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290478

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