StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethyl Sulfoxide → Rac. 2-cyano-4-(5-acetoxy-2-hydroxy-3,4,6,-trimethylphenyl)-butan-2-ol

HRID 1415230
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1415230
[C:1]([O:4][C:5]1[C:6]([CH3:19])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([OH:18])([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].CS(C)=O.[C-:24]#[N:25].[K+].OS(O)(=O)=O>O.C(OCC)C>[C:24]([C:10]([OH:18])([CH2:9][CH2:8][C:7]1[C:6]([CH3:19])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]=1[OH:11])[CH3:17])#[N:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 144156666-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

Produkt 1

HCID 21432304Rac. 2-cyano-4-(5-acetoxy-2-hydroxy-3,4,6,-trimethylphenyl)-butan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 26.4 g. (0.1 mol.) of (±)-6-acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman in 200 ml. of dimethylsulfoxide was rapidly stirred as 32.5 g. (0.5 mol.) of granular KCN was added by sifting so that a uniformly dispersed suspension was obtained. The resulting mixture was cooled to 15 degrees centigrade as 47.0 ml. of 12N aqueous H2SO4 was added over 1.25 hours as the internal temp. was maintained at 20° centigrade. Tlc at this point showed a major, slower-running spot in addition to traces of starting material. The material was poured into diethylether and H2O. The ether solutions were washed with water and brine, dried over NaSO4 and stripped of solvent to yield (±)-2-cyano-4-(5-acetoxy-2-hydroxy-3,4,6-trimethylphenyl)butan-2-ol as a gum.

Aufarbeitung

  1. filtrationby sifting so that a uniformly dispersed suspension
  2. customwas obtained
  3. temperatureThe resulting mixture was cooled to 15 degrees centigrade as 47.0 ml
  4. temperaturewas maintained at 20° centigrade
  5. additionin addition to traces of starting material
  6. washThe ether solutions were washed with water and brine
  7. dry with materialdried over NaSO4

Quellen und Nachweise

ORD-Eintrag
ord-f71c60466ec84b29a25e5a7630a538df
Quelldatensatz
uspto-grants-1977_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04003919

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion