Reaktion #447096

Reaktionsgleichung

α-cyanobenzyl alcohol

hydrogen cyanide

benzaldehyde

→

(R)-(+)-α-cyanobenzyl alcohol

Ausbeute 55.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter evaporating volatile components off in the same manner as in Example 1
2. 2
   workup.ADDITIONto the residue, dichloromethane (20 ml) was added
3. 3
   workup.STIRRINGstirred at room temperature
4. 4
   Sonstigeto obtain a homogeneous solution
5. 5
   TemperaturAfter cooling the resulting solution to 0° C.
6. 6
   workup.STIRRINGstirred at room temperature for 15 hours
7. 7
   workup.ADDITIONThereafter, the reaction mixture was treated in the same manner as in Example 1
8. 8
   Sonstigewas produced in the yield of 55% which

Vorschrift

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%.

Quelle