Reaktion #1050757

Reaktionsgleichung

H2SO4

LiAlH4

THF

dimethyl 4,4'-biphenyldicarboxylate

THF

H2O

→

4,4-Bis(hydroxymethyl)biphenyl

Ausbeute 93.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 1000 ml three-necked flask, fitted with an efficient condenser
2. 2
   TemperaturThe mixture is refluxed
3. 3
   SonstigeThe THF is evaporated under reduced pressure
4. 4
   Sonstigeto give
5. 5
   workup.ADDITIONa suspension of colourless product in aqueous acid
6. 6
   FiltrationThe product is filtered
7. 7
   Waschenwashed with H2O
8. 8
   SonstigeAfter recrystallisation from aceton, white crystals
9. 9
   Sonstigeare obtained

Vorschrift

In a 1000 ml three-necked flask, fitted with an efficient condenser, a thermometer and a dropping funnel, is placed a suspension of 6,2 g (0.144 mol) LiAlH4 in 80 ml dry THF under an inert atmosphere. A solution of 30 g (0.122 mol) dimethyl 4,4'-biphenyldicarboxylate in 250 ml dry THF is added dropwise over a period of 30 minutes. The mixture is refluxed with stirring for 1 hour. The mixture is cooled to -20° C. and 80 ml of H2O is added dropwise, followed by slow addition of 80 ml of 20% H2SO4 (aq.). The THF is evaporated under reduced pressure to give a suspension of colourless product in aqueous acid. The product is filtered and washed with H2O. After recrystallisation from aceton, white crystals are obtained. Yield: 93%; melting point: 187.3° C.-188.5° C.

Quelle