Dimethylformamide → HCID 15401124, compound

Participants

Reaction Conditions

Reaction Steps

To a 500 mL round-bottomed flask were added 1,5-dihydroxynaphthalene (15.0 g, 0.094 mol), potassium carbonate (27.2 g, 0.2 mol), n-hexylbromide (32.5 g, 0.2 mol), and 200 mL of DMF. The reaction was heated to 90° C. overnight, cooled to room temperature, and poured into 700 mL of water. The dark brown precipitate was filtered and washed with methanol. The crude product was refluxed in methanol and then filtered to give light green solid 25.2 g (80% yield). 1H NMR (CDCl3) δ (ppm): 0.92 (t, J=6.5 Hz, 6H), 1.35-1.41 (m, 8H), 1.52-1.57 (m, 4H), 1.85-1.92 (m, 4H), 4.10 (t, J=6.4 Hz, 4H), 6.81 (d, J=7.6 Hz, 2H), 7.30-7.36 (m, 2H), 7.84 (d, J=8.3 Hz); M.p. 92-93° C.

Provenance & Evidence