1: 4-hydroxy-benzonitrile With sodium hydride in mineral oil T=20°C; 0.5 h; Schlenk techniqueInert atmosphere; 2: 1,6-dibromo-n-hexane in mineral oil 2 h; Schlenk techniqueInert atmosphere;

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1: 1.) n-butyllithium / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) THF, a) -50 deg C, 1 h, b) 0 deg C, 3 h, c) room temp., overnight 2: 95 percent / HCl gas / diethyl ether / 0 - 20 °C 3: 1.) TEA / 1.) CH2Cl2, 1 h, 2.) 120 deg C, 1.5 h View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 30 min, 2.) THF, hexane, RT, overnight 2: 92 percent / conc. aq. H2SO4 / 6 h / Heating View Scheme

1: 1.) n-butyllithium / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) THF, a) -50 deg C, 1 h, b) 0 deg C, 3 h, c) room temp., overnight 2: 95 percent / HCl gas / diethyl ether / 0 - 20 °C 3: 1.) TEA / 1.) CH2Cl2, 1 h, 2.) 120 deg C, 1.5 h 4: 1.) 60 percent NaH / 1.) THF, reflux, 15 min, 2.) THF, RT, overnight View Scheme

1: 1.) n-butyllithium / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) THF, a) -50 deg C, 1 h, b) 0 deg C, 3 h, c) room temp., overnight 2: 95 percent / HCl gas / diethyl ether / 0 - 20 °C 3: 1.) TEA / 1.) CH2Cl2, 1 h, 2.) 120 deg C, 1.5 h View Scheme

1: 1.) n-butyllithium / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) THF, a) -50 deg C, 1 h, b) 0 deg C, 3 h, c) room temp., overnight 2: 95 percent / HCl gas / diethyl ether / 0 - 20 °C 3: 1.) TEA / 1.) CH2Cl2, 1 h, 2.) 120 deg C, 1.5 h View Scheme

1: 1.) n-butyllithium / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) THF, a) -50 deg C, 1 h, b) 0 deg C, 3 h, c) room temp., overnight 2: 95 percent / HCl gas / diethyl ether / 0 - 20 °C 3: 1.) TEA / 1.) CH2Cl2, 1 h, 2.) 120 deg C, 1.5 h View Scheme

1: 1.) n-butyllithium / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) THF, a) -50 deg C, 1 h, b) 0 deg C, 3 h, c) room temp., overnight 2: 95 percent / HCl gas / diethyl ether / 0 - 20 °C 3: 1.) TEA / 1.) CH2Cl2, 1 h, 2.) 120 deg C, 1.5 h View Scheme