Reaktion #1533995

Reaktionsgleichung

n-butyllithium

water

4-dimethylaminocyclohexanone

2-bromodiphenylmethane

n-butyllithium

→

1-[2-(phenylmethyl)phenyl]-4-dimethylaminocyclohexanol

Ausbeute 30.6%

Lösungsmittel

hexane

THF

hexane

THF

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwith stirring
2. 2
   Temperaturwhile maintaining the temperature below -40° C
3. 3
   workup.STIRRINGfurther stirred under N2 atmosphere overnight (16 hours) at room temperature
4. 4
   SonstigeThe aqueous phase of the resultant mixture is removed
5. 5
   Sonstigethe product crystallized out of the organic phase
6. 6
   FiltrationAfter filtration (
7. 7
   Waschenwashing the filter cake with hexane) the organic phase
8. 8
   Waschenis washed three times with 100°ml portions of water
9. 9
   Temperaturcooled overnight
10. 10
    SonstigeA second crop is obtained
11. 11
    Sonstigerecrystallized from 50 ml of toluene

Vorschrift

To 24.7 g of 2-bromodiphenylmethane and 100 ml of dry tetrahydrofuran (THF, hereinafter) is added 55 ml of 2.4 molar solution of n-butyllithium in hexane dropwise with stirring at -40° to 50° C. under a dry nitrogen atmosphere. The resultant solution is stirred one hour after addition of the n-butyllithium is completed. A solution of 15.5 g 4-dimethylaminocyclohexanone in 50 ml of dry THF is added dropwise with stirring while maintaining the temperature below -40° C. The resultant solution is stirred at -40°0 to -50° C. for two hours after addition of the ketone is completed and further stirred under N2 atmosphere overnight (16 hours) at room temperature. The solution is cooled to 0° C. and 350 ml of water and 400 ml of hexane are added thereto. The aqueous phase of the resultant mixture is removed and the product crystallized out of the organic phase. After filtration (washing the filter cake with hexane) the organic phase is washed three times with 100°ml portions of water and cooled overnight. A second crop is obtained, combined with the first crop and recrystallized from 50 ml of toluene to yield 9.46 g (30.6% yield) of 1-[2-(phenylmethyl)phenyl]-4-dimethylaminocyclohexanol, m.p. 140°-141° C.

Quelle