Reaktion #449130

Reaktionsgleichung

1-phenyl-1-indanol

1-Indanone

PhMgBr

→

desired product

Ausbeute 95.9%

1-Phenylindene

Ausbeute 95.9%

Lösungsmittel

diethylether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturto slowly warm to 20°-25° C.
3. 3
   SonstigeAfter the reaction period the mixture
4. 4
   workup.ADDITIONwas poured on ice
5. 5
   Extraktionextracted with aqueous solutions of 1M HCI (1×100 mL), 1M NaHCO3 (1×100 mL), andthen H2O (1×100 mL)
6. 6
   TrocknenThe organic layer was then dried over MgSO4
7. 7
   FiltrationFiltration
8. 8
   Sonstigefollowed by removal of the volatiles
9. 9
   Sonstigeresulted in the isolation of a yellow oil which by NMR
10. 10
    workup.DISTILLATIONThis oil was then distilled under vacuum

Vorschrift

1-Indanone (13.30 g, 0.1006 moles) was stirred in diethylether (300 mL) at -78° C. as PhMgBr (0.150 moles, 50.00 mL of 3.0M solution in diethylether) was added. The mixture was then allowed to slowly warm to 20°-25° C. and then stirred 16 hours. After the reaction period the mixture was poured on ice and then extracted with aqueous solutions of 1M HCI (1×100 mL), 1M NaHCO3 (1×100 mL), andthen H2O (1×100 mL). The organic layer was then dried over MgSO4. Filtration followed by removal of the volatiles resulted in the isolation of a yellow oil which by NMR was seen to still contain some 1-phenyl-1-indanol. This oil was then distilled under vacuum to yield the desired product as a pale yellow oil (18.56 g, 95.9 percent).

Quelle