Sodium Cyanide → 1-Phenyl-1-cyclohexyl-3-cyano-1-propanol

HRID 1074149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074149
[C:1]1([C:7]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)([OH:11])[CH2:8][CH2:9]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:18]#[N:19].[Na+]>CS(C)=O>[C:1]1([C:7]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)([OH:11])[CH2:8][CH2:9][C:18]#[N:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 138411961-Phenyl-1-cyclohexyl-3-chloro-1-propanol

Produkt 1

HCID 221558721-Phenyl-1-cyclohexyl-3-cyano-1-propanolAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 1-phenyl-1-cyclohexyl-3-chloro-1-propanol (3.8 g) and sodium cyanide (0.69 g) in 11 ml of dimethyl sulphoxide (DMSO) was heated at 140° C. for 3 hours. The mixture was poured into ice, then the water was extracted with ether. The solvent was removed and the residue triturated with diisopropylic ether to afford 2.7 g of 1-phenyl-1-cyclohexyl-3-cyano-1-propanol. M.p. 97°-101° C.

Aufarbeitung

  1. additionThe mixture was poured into ice
  2. extractionthe water was extracted with ether
  3. customThe solvent was removed
  4. customthe residue triturated with diisopropylic ether

Quellen und Nachweise

ORD-Eintrag
ord-8c8207ee99334e31a346fd532bb00ef3
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04973592

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