p-Toluenesulfonic acid → HCID 71245667, Verbindung

HRID 575500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 575500
[CH3:1][O:2][C:3]1[C:4]2[S:20][CH:19]=[CH:18][C:5]=2[C:6]2[CH:7]=[C:8]([O:16][CH3:17])[C:9]3[S:15][CH:14]=[CH:13][C:10]=3[C:11]=2[CH:12]=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.[CH2:32]([CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])CO)[CH2:33][CH2:34][CH3:35].[CH3:45][CH2:46][CH2:47][CH2:48]CC>CCCCCC.ClCCl>[CH2:45]([CH:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:21][CH3:31])[CH2:17][O:16][C:8]1[C:9]2[S:15][CH:14]=[CH:13][C:10]=2[C:11]2[CH:12]=[C:3]([O:2][CH2:1][CH:36]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:4]3[S:20][CH:19]=[CH:18][C:5]=3[C:6]=2[CH:7]=1)[CH2:46][CH2:47][CH3:48]

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 8058HexaneHCID 198002-Butyl-1-octanolHCID 71245552HCID 71245552, Verbindung

Produkt 1

HCID 71245667HCID 71245667, VerbindungAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226440Methylenechloride HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

Compound 7 (1.80 g, 6.0 mmol), 1.14 g (6.0 mmol) of toluene-4-sulfonic acid (CH3C6H4SO3H.H2O), and 35 mL of 2-butyloctanol were added into a 250 mL 3-neck flask equipped with a ondenser. The system was heated at 180° C. overnight under argon before the mixture was cooled down to room temperature. Hexane (200 mL) was added and the organic layer was washed with saturated NaHCO3 before the solvent was removed under vacuum. Excess 2-butyloctanol was distilled out under vacuum. Column chromatography (silica gel) with an eluent of hexane/dichloromethane (v/v, 100/4) yielded product BB-4 as a colorless liquid (2.5 g, ˜68.5% yield). 1H NMR (CDCl3, 500 MHz): δ 7.96 (d, 2H, J=5.5 Hz), δ 7.60 (d, 2H, J=5.5 Hz), δ 7.50 (s, 2H), δ 4.23 (d, 4H, J=5.5 Hz), δ 1.99 (m, 2H), δ 1.33 (m, 32H), δ 0.96 (t, 6H, J=7.0 Hz), δ 0.90 (t, 6H, J=7.0 Hz).

Aufarbeitung

  1. customequipped with a ondenser
  2. temperaturewas cooled down to room temperature
  3. washthe organic layer was washed with saturated NaHCO3 before the solvent
  4. customwas removed under vacuum
  5. distillationExcess 2-butyloctanol was distilled out under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bf230322e9ab46d48f7cc0fca0d8ab85
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09035004B2

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