Pyridine → HCID 23125916, Verbindung

HRID 132727

Reaktionsgleichung

Reaktionsgleichung von HRID 132727
[OH:1][CH2:2][C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.N1C=C[CH:26]=[CH:25][CH:24]=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O>[C:22]([O:1][CH2:2][C:3]1([CH2:16][O:17][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 3450229H-Fluorene-9,9-dimethanol

Produkt 1

HCID 23125916HCID 23125916, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 11.3 g (0.05 mol) 9,9-dihydroxymethylfluorene was added 50 ml tetrahydrofuran, then added 12.1 ml (0.15 mol) pyridine with stirring. To the resulting homogenous mixture was slowly added 14.5 ml (0.125 mol) benzoyl chloride. The mixture was stirred at room temperature for 1 hour, and then heated refluxing for 4 hours. Upon reaction completion, 70 ml water was added to dissolve the resulting salt. The mixture was extracted with toluene. The organic phase was separated, washed with saturated saline for two times, dried over anhydrous sodium sulfate. The solvent was removed to give a white solid. Recrystallization from ethyl acetate gave 9,9-bis(benzoyloxymethyl)fluorene as a white crystal, the yield was 89%, and m.p. was 144-146° C. 1HNMR: δ (ppm) 4.74(s, 4H, CH2), 7.25-7.75(m, 18H, ArH)

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. temperatureheated
  3. temperaturerefluxing for 4 hours
  4. additionwas added
  5. dissolutionto dissolve the resulting salt
  6. extractionThe mixture was extracted with toluene
  7. customThe organic phase was separated
  8. washwashed with saturated saline for two times
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed
  11. customto give a white solid
  12. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a7d2e366e4a44ea7acb857e3294796d8
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388061B2

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