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

HRID 1287952
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1287952
[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 2.4 g. (0.1 mol.) of rac. 6-acetoxy-2-hydroxy-2.5,7,8-tetramethylchroman in a total of 200 ml. of dimethyl-sulfoxide was rapidly stirred as 32.5 g. (0.5 mol.) of granular KCN was added thereto by sifting so that a uniformly dispersed suspension was obtained. The resulting suspension was cooled to 15° centigrade as 47.0 ml of 12N aqueous H2SO4 was added over 1.25 hrs. as the internal temp. was maintained at 20 degrees centigrade. Tlc at this point showed a major, slowerrunning spot in addition to trace of starting material. The material was poured into diethylether and H2O. The ether soulutions were washed with water and brine, dried over NaSO4 and stripped of solvent to yield rac. 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. additionwas added over 1.25 hrs
  4. temperaturewas maintained at 20 degrees centigrade
  5. additionin addition to trace of starting material
  6. washThe ether soulutions were washed with water and brine
  7. dry with materialdried over NaSO4

Quellen und Nachweise

ORD-Eintrag
ord-79c1fa33611840b59ba76a565eebca9e
Quelldatensatz
uspto-grants-1976_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03986980

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