반응 #1148664

반응 방정식

2-indanone

phenylmagnesium bromide

HCl

water

→

crystals

수율 64.3%

2-Phenylindene

수율 64.3%

용매

benzene

benzene

—

hexanes

반응 조건

후처리

1. 1
   온도The solution was cooled to 0° C.
2. 2
   세척washed with brine (2×100 mL)
3. 3
   추출The aqueous layer was extracted with hexanes (2×50 mL)
4. 4
   건조the combined organic layers were dried (MgSO4)
5. 5
   여과filtered
6. 6
   기타the solvent removed in vacuo from the filtrate
7. 7
   기타to yield a brown oil
8. 8
   workup.ADDITIONcontaining 4 Å molecular sieves
9. 9
   온도After refluxing for 2.5 hours
10. 10
    여과the solution was filtered
11. 11
    온도cooled to 5° C. overnight
12. 12
    여과The product, a white flaky solid, was collected by filtration
13. 13
    세척was washed with 50 mL of cold benzene
14. 14
    기타Additional product is obtained
15. 15
    농축by concentrating the filtrate
16. 16
    온도cooling

실험 절차

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.

출처