Thionyl Chloride → 3,3,3-Triphenylpropan-1-ol

Beteiligte Stoffe

Reaktionsschritte

To an ethanol solution (300 ml) of 3,3,3-triphenylpropionic acid (15 g) was added dropwise, under ice-cooling, thionyl chloride (5 ml). The mixture was refluxed for 12 hours. The reaction mixture was cooled and concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate, which was washed with water, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution. The organic layer was dried, which was then concentrated under reduced pressure. The concentrate was dissolved in ether (50 ml), which was added dropwise, under ice-cooling, to an ether suspension (250 ml) of lithium aluminum hydride (1.89 g). The mixture was stirred for one hour at room temperature, which was processed with 10% HCl, followed by addition of ether. The organic layer was washed with water, dried and concentrated under reduced pressure (14.2 g).

Herkunft & Nachweise