반응 #1909801

반응 방정식

9-fluorenone-4-carbonyl chloride

diethylene glycol

triethylamine

→

fluorenone

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타equipped with a reflux condenser and a mechanical stirrer
2. 2
   온도The solution was refluxed for 6 hours
3. 3
   여과filtered hot
4. 4
   기타to remove triethylamine hydrochloride salt byproduct
5. 5
   기타the filtrate was evaporated to dryness
6. 6
   기타to obtain the crude product
7. 7
   기타The crude product was recrystallized from ethyl acetate with activated charcoal
8. 8
   기타The product was dried at 60° C. in a vacuum oven for 6 hours

실험 절차

A 10.0 g quantity of 9-fluorenone-4-carbonyl chloride (0.04 mole, obtained from Aldrich Chemicals Co, Milwaukee, Wis. 53201, USA) and 100 ml of tetrahydrofuran (obtained from Aldrich) were added to a 250 ml, 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The solution was stirred for about ½ hour, and then 2.186 g of diethylene glycol (0.02 mole, obtained from Aldrich) in 50 ml of tetrahydrofuran were added, followed by the addition of 4.17 g of triethylamine (0.04 mole, obtained from Aldrich). The solution was refluxed for 6 hours, filtered hot to remove triethylamine hydrochloride salt byproduct, and the filtrate was evaporated to dryness to obtain the crude product. The crude product was recrystallized from ethyl acetate with activated charcoal. The product was dried at 60° C. in a vacuum oven for 6 hours to yield a third dimeric fluorenone derivative, which was a yellow solid (5.0 g, 47% yield). The product had a melting point of 137° C. A 1H-NMR (300 MHz) spectrum in CDCl3 yielded chemical shifts (ppm) of: 3.88–4.00 (t, 4H); 4.56–4.65 (t, 4H); 7.15–7.34 (m, 4H); 7.40–7.49 (td, 2H); 7.61–7.68 (d, 2H); 7.71–7.77 (dd, 2H); 7.85–7.92 (dd, 2H); 8.20–8.27 (d, 2H).

출처