Pyridine → HCID 23126022, Verbindung

HRID 132728

Reaktionsgleichung

Reaktionsgleichung von HRID 132728
[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.N1C=CC=CC=1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:33](Cl)(=[O:36])[CH2:34][CH3:35]>O.O1CCCC1>[C:24]([O:1][CH2:2][C:3]1([CH2:16][O:17][C:33](=[O:36])[CH2:34][CH3:35])[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:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

7

Edukt 4

HCID 1049Pyridine2×HCID 7412Benzoyl chlorideHCID 62324Propionyl chlorideHCID 3450229H-Fluorene-9,9-dimethanol

Produkt 1

HCID 23126022HCID 23126022, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 4.5 g (0.02 mol) 9,9-di(hydroxymethyl)fluorene were added 30 ml tetrahydrofuran, and added 3.3 ml (0.03 mol) pyridine with stirring. To the resulting homogenous mixture was added slowly 2.3 ml (0.02 mol) benzoyl chloride, and the mixture was stirred at temperature for 1 hour, then heated refluxing for 5 hours. Next, the mixture was cooled to room temperature, and 20 ml tetrahydrofuran and 3.3 ml(0.03 mol) pyridine were added with stirring. To the resulting homogenous mixture was slowly added 1.8 ml (0.02 mol) propionyl chloride, and the mixture was stirred at room temperature for 1 hour, and heated refluxing for 5 hours. Then 30 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, and dried over anhydrous sodium sulfate. The solvent was removed. Recrystallization from ethyl acetate gave 9-(benzoyloxymethyl)-9-(propionyloxymethyl)fluorene as a white crystal, and the yield was 79%. 1HNMR: δ (ppm) 1.23(t, 3H, CH3), 2.39(m, 2H, CH2), 4.48(s, 2H, COOCH2), 4.62(s, 2H, OCH2 linking with benzoyl), 7.33-8.03(m, 13H, ArH)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9ecee5bddf50403e821309d6521d6031
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388061B2

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