Reacción #1148664

Ecuación de reacción

2-indanone

phenylmagnesium bromide

HCl

water

→

crystals

Rendimiento 64.3%

2-Phenylindene

Rendimiento 64.3%

Disolventes

benzene

benzene

—

hexanes

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution was cooled to 0° C.
2. 2
   Lavadowashed with brine (2×100 mL)
3. 3
   ExtracciónThe aqueous layer was extracted with hexanes (2×50 mL)
4. 4
   Secadothe combined organic layers were dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent removed in vacuo from the filtrate
7. 7
   Otroto yield a brown oil
8. 8
   workup.ADDITIONcontaining 4 Å molecular sieves
9. 9
   TemperaturaAfter refluxing for 2.5 hours
10. 10
    Filtraciónthe solution was filtered
11. 11
    Temperaturacooled to 5° C. overnight
12. 12
    FiltraciónThe product, a white flaky solid, was collected by filtration
13. 13
    Lavadowas washed with 50 mL of cold benzene
14. 14
    OtroAdditional product is obtained
15. 15
    Concentraciónby concentrating the filtrate
16. 16
    Temperaturacooling

Procedimiento

A solution of 2-indanone (13.47 g, 102 mmol) in anhydrous benzene (100 mL) was added to phenylmagnesium bromide (3.0 M in diethyl ether, 50.9 mL. 153 mmol) at 5° C. over 2.5 hours. The reaction was allowed to warm to room temperature over 30 minutes. The solution was cooled to 0° C. and 150 mL of water are added. The resultant mixture was diluted with 200 mL of hexanes, neutralized with 5 M HCl, and washed with brine (2×100 mL). The aqueous layer was extracted with hexanes (2×50 mL), and the combined organic layers were dried (MgSO4), filtered, and the solvent removed in vacuo from the filtrate to yield a brown oil. This oil and p-toluenesulfonic acid (0.50 g) were dissolved in benzene (250 mL) in a round-bottom flask below a Soxhlet extractor containing 4 Å molecular sieves. After refluxing for 2.5 hours, the solution was filtered and cooled to 5° C. overnight. The product, a white flaky solid, was collected by filtration, and was washed with 50 mL of cold benzene. Additional product is obtained by concentrating the filtrate, cooling, and filtering the crystals (12.60 g, 64.3% yield). 1H NMR (400 MHz, 20 C, CDCl3) 7.62 (d, J=7.3 Hz, 2H), 7.47 (d, J=7.3 Hz, 1H), 7.39 (M, 3H), 7.27 (m, 2H), 7.22 (s, 1H), 7.18(t, J=7.4 Hz, 1H), 3.78(S<2H), 13C{1H} NMR (100 MHz, 20 C, CDCl3): 146.3, 145.3, 143.1, 135.9, 128.6, 127.5, 126.5, 126.4, 125.6, 124.7, 123.6, 120.9, 38.9.

Fuente