1-Indanone → 1-Phenyl-1H-indene

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).

1. additionwas added
2. temperatureto slowly warm to 20°-25° C.
3. customAfter the reaction period the mixture
4. additionwas poured on ice
5. extractionextracted with aqueous solutions of 1M HCI (1×100 mL), 1M NaHCO3 (1×100 mL), andthen H2O (1×100 mL)
6. dry with materialThe organic layer was then dried over MgSO4
7. filtrationFiltration
8. customfollowed by removal of the volatiles
9. customresulted in the isolation of a yellow oil which by NMR
10. distillationThis oil was then distilled under vacuum

ORD record

ord-b31589cc69694298b5602cf2d3cb8cc0

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05866704