Methane → 2,6-Dihexyloxy-naphthalene

A solution of sodium (3.04 g, 132 mmol) in dry methanol (60 ml) was refluxed for 30 minutes and cooled. A solution of 2,6-naphthalenediol (9.0 g, 56.2 mmol) in dry methanol (40 ml) was added and the mixture refluxed for 30 minutes and cooled. 1-Bromohexane (17.5 ml, 125 mmol) was added and the reaction mixture was refluxed under an argon atmosphere for 19 h. The solvent was evaporated and ether (250 ml) was added. It was washed with aqueous sodium hydroxide solution (10%, 100 ml) and water (2×100 ml) to yield a dark brown solution. After refluxing with activated charcoal for 30 min and filtration, the solution was evaporated to yield an oil which was recrystallised from methanol (250 ml). The fine white platelets were collected at the pump and washed with a little cold methanol to give (12) (8.33 g). A recrystallisation gave more product (0.67 g, 49% total yield), m.p. 78.0°-79.0° C., Rf 0.83 (dichloromethane), (Found: C, 80.7; H, 10.0; M+, 328.2404) C22H32O2 requires C, 80.4; H, 9.8; M, 328.2404); vmax (KBr)/cm-1 3050 w, 2900 s, 2840 s, 1590 s, 1495 m, 1455 m, 1385 s, 1375 (s), 1225 s, 1165 s, 1110 s, 1070 s, 1045 s, 995 s, 965 s, 850 s; 1HNMR (400 MHz; CDCl3) δ0.93 (6H, t, J=6.8 Hz, --CH3), 1.42-1.32 (8H, m, alkyl), 1.50 (4H, qn, J=7.3 Hz, OC2H4 --CH2), 1.84 (4H, qn, J=7.1 Hz, ArOCH2 --CH2), 4.04 (4H, t, J=6.6 Hz, O--CH2), 7.09 (2H, d, J=2.1 Hz Ar1,5 --H), 7.13 (2H, dd, J=8.8 Hz, 2.2, Ar3,7 --H), 7.62 (2H, d, J=8.9 Hz, Ar4,8 --H); δC (100 MHz; CDCl3) 14.1, 22.6, 25.8, 29.3, 31.6, 68.0, 106.9, 119.2, 128.0, 129.7, 155.5; m/z (EI) : 328 (M, 16%), 244 (13,M--C6H12), 160 (100,M-2C6H12), 131 (21), 55 (21).