تفاعل #1148664

معادلة التفاعل

2-indanone

phenylmagnesium bromide

HCl

water

→

crystals

المردود 64.3%

2-Phenylindene

المردود 64.3%

المذيبات

benzene

benzene

—

hexanes

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe solution was cooled to 0° C.
2. 2
   غسيلwashed with brine (2×100 mL)
3. 3
   استخلاصThe aqueous layer was extracted with hexanes (2×50 mL)
4. 4
   تجفيفthe combined organic layers were dried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   أخرىthe solvent removed in vacuo from the filtrate
7. 7
   أخرىto yield a brown oil
8. 8
   workup.ADDITIONcontaining 4 Å molecular sieves
9. 9
   درجة الحرارةAfter refluxing for 2.5 hours
10. 10
    ترشيحthe solution was filtered
11. 11
    درجة الحرارةcooled to 5° C. overnight
12. 12
    ترشيحThe product, a white flaky solid, was collected by filtration
13. 13
    غسيلwas washed with 50 mL of cold benzene
14. 14
    أخرىAdditional product is obtained
15. 15
    تركيزby concentrating the filtrate
16. 16
    درجة الحرارةcooling

الإجراء التجريبي

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.

المصدر