Triethylamine → Fluoreneone

A 4.85 g quantity of 9-fluorenone-4-carbonyl chloride (0.02 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 1.74 g of 1,10-decanediol (0.01 mole, obtained from Aldrich) in 50 ml of tetrahydrofuran were added, followed by the addition of 2 g of triethylamine (0.02 mole, obtained from Aldrich). The solution was refluxed for 6 hours and filtered hot to remove triethylamine hydrochloride salt by-product, and the filtrate was evaporated to dryness. A liquid product was obtained, which solidified upon standing at room temperature for a couple of hours. 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 second dimeric fluorenone derivative, which was a yellow solid (2.5 g, 43% yield). The product had a melting point of 101–102° C. A 1H-NMR spectrum (300 MHz) in CDCl3 yielded chemical shifts (ppm) as follows: 1.15–1.61 (m, 12H); 1.71–1.92 (q, 4H); 4.34–4.47 (t, 4H); 7.32–7.37 (m, 4H); 7.50 (td, 2H); 7.70 (d, 2H); 7.82 (dd, 2H); 7.93 (dd, 2H); 8.28 (d, 2H).

1. customequipped with a reflux condenser and a mechanical stirrer
2. temperatureThe solution was refluxed for 6 hours
3. filtrationfiltered hot
4. customto remove triethylamine hydrochloride salt by-product
5. customthe filtrate was evaporated to dryness
6. customA liquid product was obtained
7. waitupon standing at room temperature for a couple of hours
8. customThe crude product was recrystallized from ethyl acetate with activated charcoal
9. customThe product was dried at 60° C. in a vacuum oven for 6 hours

ORDレコード

ord-082afea31a634e438119792c1f947897

出典データセット

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07011917B2