Reaktion #613162

Reaktionsgleichung

Naphthalene-1,5-diamine

1-bromooctane

potassium carbonate

→

N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamine

Ausbeute 38.3%

Lösungsmittel

butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with water
2. 2
   Extraktionextracted with ether three times
3. 3
   WaschenThe combined organic phase was washed three times with water
4. 4
   Sonstigeevaporated
5. 5
   Sonstigeto give black oil which
6. 6
   workup.DISTILLATIONwas distilled under reduced pressure at 90° C.
7. 7
   Sonstigeto yield a black tar
8. 8
   SonstigeThis was purified with flash chromatography
9. 9
   Sonstigeto obtain colourless oil which
10. 10
    Sonstigecrystallised

Vorschrift

Naphthalene-1,5-diamine (3.14 g, 19.8 mmol), 1-bromooctane (25.25 g, 0.130 mol), potassium carbonate (11.79 g, 85.3 mmol), and potassium iodide (0.05 g, 0.30 mmol) was stirred in dry butanol (150 ml) and heated to 110° C. for 36 h. The reaction was quenched with water and extracted with ether three times. The combined organic phase was washed three times with water and evaporated to give black oil which was distilled under reduced pressure at 90° C. to yield a black tar. This was purified with flash chromatography using hexane as mobile phase to obtain colourless oil which crystallised to yield N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamine (2.3 g, 3.79 mmol) as white crystals. 1H-NMR (CDCl3, δ): 0.85 (t, 12H), 1.0-1.4 (m, 40H), 1.4-1.6 (m, 8H), 3.08 (t, 8H), 7.1 (d, 2H), 7.35 (t, 2H), 8.01 (d, 2H) MS MALDI-TOF (m/z): 606.574

Quelle