Reaktion #613163

Reaktionsgleichung

1,5-dihydroxynaphthalene

1-bromooctane

potassium carbonate

→

1,5-bis(octyloxy)naphthalene

Ausbeute 140.2%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe potassium carbonate was filtered off
2. 2
   Sonstigethe reaction mixture was quenched with water
3. 3
   Extraktionextracted two times with ether
4. 4
   WaschenThe combined organic phase was then washed once with 1M HCl, two times with water
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residual brown solid was recrystallised in ethanol

Vorschrift

1,5-dihydroxynaphthalene (2.95 g, 18.4 mmol), 1-bromooctane (8.2 g, 42.5 mmol), and potassium carbonate (50 g, 0.36 mol) was mixed in N,N-dimethylformamide and heated at 90° C. for 5 h. The potassium carbonate was filtered off and the reaction mixture was quenched with water and extracted two times with ether. The combined organic phase was then washed once with 1M HCl, two times with water, and evaporated. The residual brown solid was recrystallised in ethanol to form 1,5-bis(octyloxy)naphthalene (4.96 g, 12.9 mmol) as brown crystals. 1H-NMR (CDCl3, δ): 0.89 (t, 6H), 1.2-1.4 (m, 16H), 1.4-1.6 (m, 4H), 1.91 (m, 4H), 4.12 (t, 4H), 6.81 (d, 2H), 7.34 (t, 2H), 7.83 (d, 2H) MS MALDI-TOF (m/z): 384.266

Quelle