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Potassium Carbonate → HCID 59560832, Verbindung

HRID 1176964
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1176964
[C:1]([O-])([O-])=O.[K+].[K+].[CH2:7]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:23]=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>O1CCOCC1.O>[CH2:29]([O:28][C:27]1[CH:26]=[CH:25][C:22]([CH:23]=[CH2:1])=[CH:21][C:20]=1[O:19][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 27249313,4-Bis(dodecyloxy)benzaldehyde

Produkt 1

HCID 59560832HCID 59560832, VerbindungAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A round bottom flask was charged with Ph3PMeBr (8.79 g, 24.6 mmol), K2CO3 (3.4 g, 24.6 mmol), and 3,4-bis-dodecyloxy-benzaldehyde (10.0 g, 21.1 mmol) in a mixture of 25 mL of 1,4-dioxane and 0.3 mL of H2O. The reaction mixture was refluxed at 95° C. for 24 h. The reaction mixture was allowed to cool down to room temperature and extracted with CH2Cl2. The organic layer was washed with H2O and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give an off-white solid. The crude product was purified by column chromatography (silica gel, hexanes:dichloromethane=2:1 (v/v)) to give a white solid (6.53 g, 65.6%). 1H NMR (300 MHz, CDCl3, δ): 6.96 (d, J=1.9 Hz, 1H), 6.90 (dd, J=8.0 Hz, 1.9 Hz, 1H), 6.80 (d, J=8.2 Hz, 1H), 6.62 (dd, J=17.3 Hz, 10.7 Hz, 1H), 5.57 (dd, J=17.6 Hz, 0.5 Hz, 1H), 5.11 (d, J=11.5 Hz, 1H), 3.98 (q, J=6.6 Hz, 4H), 1.74-1.85 (m, 4H), 1.19-1.50 (m, 36H), 0.87 (t, J=6.6 Hz, 6H). 13C{1H} NMR (75 MHz, CDCl3, δ): 149.01, 148.98, 136.44, 130.63, 119.46, 113.44, 111.50, 111.18, 69.24, 32.00, 29.78, 29.72, 29.51, 29.45, 29.38, 29.34, 26.12, 22.78, 14.22. HRMS-EI (m/z): [M]+ calcd for C32H56O2, 472.4280; found, 472.4267. Anal. Calcd C32H56O2: C, 81.29; H, 11.94. Found: C, 81.36; H, 11.99.

Aufarbeitung

  1. temperatureto cool down to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customto give an off-white solid
  7. customThe crude product was purified by column chromatography (silica gel, hexanes:dichloromethane=2:1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-37d1f87ced7d4d0dbac4d0ab75eee2af
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842830B2

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