Acetone → DBF

HRID 2229100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229100
[CH:1]1[CH:2]=[CH:3][C:4]([C:23]([OH:25])=[O:24])=[C:5]([C:7]2[C:17]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:16]=3[O:15][C:14]3[C:8]=2[CH:9]=[CH:10][C:11]([CH:13]=3)=[O:12])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](Cl)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[CH3:40][C:41]([CH3:43])=O>CN(C)C=O>[CH:36]1[CH:37]=[CH:38][C:33]([CH2:32][O:12][C:11]2[CH:10]=[CH:9][C:8]3[C:7]([C:5]4[C:4]([C:23]([O:25][CH2:40][C:41]5[CH:43]=[CH:5][CH:6]=[CH:1][CH:2]=5)=[O:24])=[CH:3][CH:2]=[CH:1][CH:6]=4)=[C:17]4[C:16]([O:15][C:14]=3[CH:13]=2)=[CH:21][C:20](=[O:22])[CH:19]=[CH:18]4)=[CH:34][CH:35]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Produkt 1

HCID 371436DBF

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Fluorescein (40 g, 120.5 mmol) was dissolved in dimethylformamide (DMF, 500 mL) in a 2 L flask fitted with a mechanical stirrer then potassium carbonate (72 g, 521.7 mmol) was added in as a single portion. The reaction was heated to 80° C. then benzyl chloride (42 mL, 363.5 mmol) was added dropwise. After 24 h at 80° C. the reaction was cooled down to room temperature. Acetone (400 mL) was added and the product was allowed to precipitate overnight. The solid orange product was filtered, washed with acetone and dried in a vacuum oven at 50° C. The O-benzylfluorescein benzyl ester was obtained as an orange solid (36.4 g, 59%): mp 192-193° C. (Lit. 193-194° C.); 1H NMR (DMSO-d6): 4.97 (dd, 2H, J=12.2 Hz, J=15.3 Hz), 5.28 (s, 2H), 6.13 (d, 1H, J=1.9 Hz), 6.36 (dd, 1H, J=9.9 Hz), 6.77 (d, 1H, J=9.9 Hz), 6.82 6.77 (d, 1H, J=9.0 Hz), 6.90-6.98 (m, 3H), 7.14-7.27 (m, 4H), 7.33-7.52 (m, 6H), 7.78 (dt, 1H, J=1.65 Hz, J=7.4 Hz), 8.23 (dd, 1H, J=1.35 Hz, J=7.7 Hz); 13C NMR (DMSO-d6): 67.4, 70.7, 101.9, 105.2, 114.7, 115.0, 117.3, 128.3, 128.5, 128.7, 128.8, 128.9, 129.4, 130.0, 130.2, 130.6, 130.8, 131.2, 131.4, 133.8, 134.1, 135.3, 136.6, 150.1, 153.9, 158.7, 163.3, 165.5, 184.4; IR (nujol) cm−1 1728, 1643, 1595, 1517, 1462, 1377, 1261, 1211, 1081, 855. C34H24O5: Calc.(C, 79.67; H, 4.72) Found (C, 79.74; H, 4.79).

Aufarbeitung

  1. customfitted with a mechanical stirrer
  2. temperatureAfter 24 h at 80° C. the reaction was cooled down to room temperature
  3. customto precipitate overnight
  4. filtrationThe solid orange product was filtered
  5. washwashed with acetone
  6. customdried in a vacuum oven at 50° C

Quellen und Nachweise

ORD-Eintrag
ord-b7614599a773446caf015d8577b37e98
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420131B1

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