Diethylene Glycol → Fluoreneone

HRID 1822619

Reaktionsgleichung

Reaktionsgleichung von HRID 1822619
[CH:1]1[C:13]2[C:12](=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4](C(Cl)=O)=[CH:3][CH:2]=1.C(O)C[O:20]CCO.C(N(CC)CC)C>O1CCCC1>[C:1]1(=[O:20])[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 8117Diethylene GlycolHCID 8471TriethylamineHCID 6101429-Fluorenone-4-carbonyl chloride

Produkt 1

HCID 22281833Fluoreneone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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 byproduct
  5. customthe filtrate was evaporated to dryness
  6. customto obtain the crude product
  7. customThe crude product was recrystallized from ethyl acetate with activated charcoal
  8. customThe product was dried at 60° C. in a vacuum oven for 6 hours

Quellen und Nachweise

ORD-Eintrag
ord-10d27bc5409c456aa64d1df29c658226
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07037632B2

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