Reaktion #1467961

Reaktionsgleichung

sulphuric acid

4'-(trans-4-pentylcyclohexyl)-4-biphenylcarbonitrile

diisobutylaluminium hydride

→

4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxaldehyde

Ausbeute 95.0%

Lösungsmittel

toluene

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas placed at -35° C. in a sulphonation flast
2. 2
   workup.ADDITIONAfter completion of the addition
3. 3
   Temperaturfor a further 1.5 hours with gradual warming to 0° C., before it
4. 4
   Extraktionextracted three times with 150 ml of diethyl ether each time
5. 5
   WaschenThe organic phases were washed with 100 ml of 1N sulphuric acid, twice with 100 ml of water each time
6. 6
   Trocknenonce with 100 ml of saturated sodium chloride solution, dried over magnesium sulphate
7. 7
   Einengenconcentrated

Vorschrift

A solution of 10.0 g of 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarbonitrile in 150 ml of methylene chloride was placed at -35° C. in a sulphonation flast while gassing with argon and treated within 8 minutes with 40 ml of an about 1.5N solution of diisobutylaluminium hydride in toluene. After completion of the addition, the mixture was stirred for 2 hours at -35° C. and then for a further 1.5 hours with gradual warming to 0° C., before it was treated cautiously with 100 ml of 1N sulphuric acid and extracted three times with 150 ml of diethyl ether each time. The organic phases were washed with 100 ml of 1N sulphuric acid, twice with 100 ml of water each time and once with 100 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. There were obtained 9.5 g (95%) of 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxaldehyde as a colourless, crystalline mass (m.p. 115°-116° C.) which was used in the following step without further purification. Rf value [toluene/ethyl acetate (19:1)]: educt 0.65, product 0.52.

Quelle