反応 #613162

反応方程式

Naphthalene-1,5-diamine

1-bromooctane

potassium carbonate

→

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

収率 38.3%

溶媒

butanol

反応条件

後処理

1. 1
   その他The reaction was quenched with water
2. 2
   抽出extracted with ether three times
3. 3
   洗浄The combined organic phase was washed three times with water
4. 4
   その他evaporated
5. 5
   その他to give black oil which
6. 6
   workup.DISTILLATIONwas distilled under reduced pressure at 90° C.
7. 7
   その他to yield a black tar
8. 8
   その他This was purified with flash chromatography
9. 9
   その他to obtain colourless oil which
10. 10
    その他crystallised

実験手順

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

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