Reaktion #347362

Reaktionsgleichung

3-Benzoylpropionic acid

LiAlH4

H2O

→

6a

Ausbeute 80.0%

1-Phenyl-butane-1,4-diol

Ausbeute 80.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTHF was evaporated
2. 2
   workup.ADDITIONDiethylether and HCl (2M) was added
3. 3
   ExtraktionThe aqueous layer was extracted with diethylether
4. 4
   Waschenthe combined organic layers were washed with H2O, aqueous NaHCO3 (saturated) and H2O
5. 5
   SonstigeDrying
6. 6
   Filtration(MgSO4), filtration and evaporation

Vorschrift

3-Benzoylpropionic acid 11a dissolved in THF was reacted with LiAlH4 according to the general procedure. The following workup procedure was used: H2O was added and THF was evaporated. Diethylether and HCl (2M) was added. The aqueous layer was extracted with diethylether and the combined organic layers were washed with H2O, aqueous NaHCO3 (saturated) and H2O. Drying (MgSO4), filtration and evaporation gave 80% yield of 6a. 1H-NMR: 7.35-7.22 (m, 5H, Ar--H); 4.70 (t, 1H, CH--OH); 3.64 (t, 2H, CH2OH); 3.10 (brs, 1H, CH--OH); 2.60 (brs, 1H, CH2 --OH); 1.84 (q, 2H, CH2 --CHOH); 1.72-1.61 (m, 2H, CH2CH2OH).

Quelle