Benzaldehyde → Mandelonitrile, (+)-

HRID 359914

Reaktionsgleichung

Reaktionsgleichung von HRID 359914
C#N.C(=O)C1C=CC=CC=1.[C:11]([CH:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[N:12]>ClCCl.[Ti]>[C:11]([C@H:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[N:12]

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 768Hydrogen CyanideHCID 10758Mandelonitrile

Produkt 1

HCID 9548674Mandelonitrile, (+)-Ausbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23963TitaniumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of L(+)-diethyl tartarate (412 mg) in absolute dichloromethane (20 ml), tetaraisopropyl titanate (568 mg) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, to the residue, dichloromethane (20 ml) was added and stirred at room temperature to obtain a homogeneous solution. After cooling the resulting solution to 0° C., hydrogen cyanide (0.4 ml) and then benzaldehyde (212 mg) were added and stirred at room temperature for 15 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 1 and analyzed by HPLC to reveal that α-cyanobenzyl alcohol was produced in the yield of 55% which contained the R(+) isomer with the enantiomer excess percentage of 77%.

Aufarbeitung

  1. customAfter evaporating volatile components off in the same manner as in Example 1
  2. additionto the residue, dichloromethane (20 ml) was added
  3. stirringstirred at room temperature
  4. customto obtain a homogeneous solution
  5. temperatureAfter cooling the resulting solution to 0° C.
  6. stirringstirred at room temperature for 15 hours
  7. additionThereafter, the reaction mixture was treated in the same manner as in Example 1
  8. customwas produced in the yield of 55% which

Quellen und Nachweise

ORD-Eintrag
ord-0da8112aec424316aed76fc8b55c3ac9
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05003083

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