Reaktion #1051958

Reaktionsgleichung

AlCl3

toluene

13

(±)-2-(2-phenylbenzyl)butyric acid

thionyl chloride

HCl

→

14

Ausbeute 85.0%

(±)-2-Ethyl-4-phenyl-1-indanone

Ausbeute 85.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeExcess thionyl chloride was removed at 10 mbar
2. 2
   workup.DISSOLUTIONby repeated dissolution in 200 cm3 of toluene in each case
3. 3
   SonstigeThe organic phase was separated off
4. 4
   Extraktionthe aqueous phase was then extracted three times with 200 cm3 of Et2O in each case
5. 5
   WaschenThe combined organic phases were washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
6. 6
   Trocknensubsequently dried (MgSO4)

Vorschrift

A solution of 236 g (0.93 mol) of 13 in 81 cm3 (1.2 mol) of thionyl chloride was stirred at room temperature for 18 hours. Excess thionyl chloride was removed at 10 mbar and the oily residue was freed from adhering residues of thionyl chloride by repeated dissolution in 200 cm3 of toluene in each case and stripping off in vacuo. The acid chloride was taken up in 400 cm3 of toluene and added dropwise at 10° C. to a suspension of 133 g (1.0 mol) of AlCl3 in 2000 cm3 of toluene. The reaction mixture was heated at 80° C. for 1 hour, poured into 2000 g of ice and acidified to pH 1 by means of concentrated aqueous HCl. The organic phase was separated off, and the aqueous phase was then extracted three times with 200 cm3 of Et2O in each case. The combined organic phases were washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution and subsequently dried (MgSO4), giving 187 g (85%) of 14, which was reacted further without further purification.

Quelle