Water → HCID 22412553, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,5-bis(iodomethyl)-2,6-dihexyloxynaphthalene (0.50 g, 0.83 mmol) and sodium cyanide (0.16 1.74 mmol) was stirred in DMF (50 ml) at 55° C. for 1 g, h. Water (50 ml) was added to the cooled mixture and the resulting precipitate was filtered, washed with water and dried. It was redissolved in a minimum of dichloromethane, hexane (40 ml) was added, and the solution was cooled to -4° C. overnight. The product was filtered to yield (14) (0.21 g, 63%), m.p. 135°-6° C.; 1H NMR (250.1 MHz, CDCl3) δ0.9-1.9 (22H, m, alkyl), 4.11 (4H, s, CH2CN), 4.14 (3H, t, J=7 Hz, CH2O), 7.35 and 7.88 (2H, 2d, J- 10 Hz, aromatic); 13C NMR. (62.9 Mhz, CDCl3) δ13.5, 14.2, 22.8, 25.9, 29.6, 31.7, 69.8, 112.2, 115.8, 118.3, 121.5, 127.9, 152.9; IR (KBr) vmax /cm-1 2248 w, 1598 s, 1261 s, 1067 s, 802 m. m/z 406 (M, 28), 238 (100), 91 (95).

Provenance & Evidence