Water → 2,6-Dihexyloxy-naphthalene

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Reaction Steps

2,6-Dihydroxynaphthalene (30.0 g, 0.19 mol) reacted with n-hexylbromide (97.5 g, 0.59 mol) in the presence of potassium carbonate (81.6 g, 0.59 mol) in 400 mL of DMF at 90° C. overnight. The reaction was poured into 700 mL of water and the precipitate was filtered, washed with water and methanol, and dried. The crude product was recrystallized from methanol to give light gray solid 41.3 g (67% yield). 1H NMR CDCl3) δ (ppm): 0.91 (t, J=6.9 Hz, 6H), 1.32-1.40 (m, 8H), 1.44-1.54 (m, 4H), 1.77-2.86 (m, 4H), 4.02 (t, J=6.6 Hz, 4H), 7.06-7.12 (m, 4H), 7.60 (d, J=8.8 Hz, 2H); M.p. 78-79° C.

Provenance & Evidence