Reaktion #50527

Reaktionsgleichung

lithium aluminum hydride

ethyl 4,4'-dimethylbiphenyl-3-carboxylate

sodium sulfate

→

3-hydroxymethyl-4,4'-dimethylbiphenyl

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Sonstigeto slowly rise to room temperature
3. 3
   FiltrationThe mixture was filtered
4. 4
   Sonstigethe solvent evaporated from the filtrate under reduced pressure
5. 5
   Sonstigethe residue flash-chromatographed on silica gel
6. 6
   Wascheneluting with 25% ethyl acetate in heptane

Vorschrift

To a suspension of lithium aluminum hydride (0.2 g) in 50 ml of ether at 0° C. was added dropwise a solution of ethyl 4,4'-dimethylbiphenyl-3-carboxylate (2 g) in ether. After the addition was complete, the mixture was allowed to slowly rise to room temperature, and stirred for 2 hours. Excess reagent was hydrolysed with wet sodium sulfate. The mixture was filtered, the solvent evaporated from the filtrate under reduced pressure, and the residue flash-chromatographed on silica gel, eluting with 25% ethyl acetate in heptane, to yield 3-hydroxymethyl-4,4'-dimethylbiphenyl as an oil.

Quelle