Toluene → 5,10-Bis(2-octyldodecyloxy)naphtho[2,3-b:6,7-b']dithiophene

HRID 592501

Reaktionsgleichung

Reaktionsgleichung von HRID 592501
[CH3:1][O:2][C:3]1[C:4]2[C:12]([CH:13]=[C:14]3[CH:18]=[CH:17][S:16][C:15]=13)=[C:11]([O:19][CH3:20])[C:7]1[S:8][CH:9]=[CH:10][C:6]=1[CH:5]=2.[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:28]([CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])CO)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].[C:49]1([CH3:59])[CH:54]=[CH:53][C:52](S(O)(=O)=O)=[CH:51][CH:50]=1>O>[CH2:52]([CH:53]([CH2:54][CH2:49][CH2:59][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:21][CH3:27])[CH2:20][O:19][C:11]1[C:12]2[C:4]([CH:5]=[C:6]3[CH:10]=[CH:9][S:8][C:7]=13)=[C:3]([O:2][CH2:1][CH:36]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:15]1[S:16][CH:17]=[CH:18][C:14]=1[CH:13]=2)[CH2:51][CH2:50][CH2:14][CH2:15][CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 214142-OctyldodecanolHCID 683593795,10-Dimethoxynaphtho[2,3-b:6,7-b']dithiophene

Produkt 1

HCID 708730075,10-Bis(2-octyldodecyloxy)naphtho[2,3-b:6,7-b']dithiopheneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Compound (3) (0.400 g, 1.33 mmol) was weighed into a flame-dried 2-neck flask fitted with a condenser. Toluene (13 mL), 2-octyl-1-dodecanol (1.59 g, 5.32 mmol), and p-toluenesulfonic acid (0.051 g, 0.266 mmol) were then added. The mixture was placed in a 130° C. heat bath and stirred overnight. The mixture was diluted with water, extracted with dichloromethane, dried over MgSO4, filtered and concentrated. The product was purified via column chromatography (10% dichloromethane in hexanes) to yield compound (4a) as a yellow solid (0.735 g, 66%). 1H NMR (500 MHz, CDCl3, 298 K): 8.46 (s, 2H); 7.45 (m, 4H); 4.27 (d, J=5.4 Hz, 4H); 2.01 (quintet, J=6.2 Hz, 2H); 1.73 (m, 4H); 1.47 (m, 60H); 0.89 (m, 12H) ppm. 13C NMR (125 MHz, CDCl3, 298 K): 149.87; 139.70; 127.98; 127.08; 124.83; 124.62; 110.84; 75.85; 39.38; 31.96; 31.42; 30.18; 29.76; 29.71; 29.43; 29.41; 27.06; 22.74; 14.18 ppm. HRMS (ESI-TOF-MS): m/z calcd for C54H88O2S2 832.6220. found 832.6217.

Aufarbeitung

  1. customfitted with a condenser
  2. customwas placed in a 130° C.
  3. temperatureheat bath
  4. extractionextracted with dichloromethane
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified via column chromatography (10% dichloromethane in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b0f7123d0cb5452280fa5d658ff199a2
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09240556B2

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