1: 1) KOH, hydroquinone / 1) ethanol,H2O, 16 h, reflux, 2) ether 2: 1) Na / 1) methanol, 30 min, 60 deg C, 2)methanol, 45 min, reflux 3: 60 percent / NaOH / methanol; H2O / 1) 12 h, r. t., 2) 6 h, reflux 4: 0.1 N (CH3)3CONa / diethyl ether; 2-methyl-propan-2-ol / 20 h / Ambient temperature 5: 61 percent / 10percent H2SO4 / methanol / 24 h / Ambient temperature 6: 1) mesitol, molecular sieve, 2) K, aniline / 1) pyridine, anh. methylcyclohexane, 10 h, irradiation, 2) liq. NH3 7: 64 percent / diisobutylaluminiumhydride / toluene View Scheme

1: 1) KOH, hydroquinone / 1) ethanol,H2O, 16 h, reflux, 2) ether 2: 1) Na / 1) methanol, 30 min, 60 deg C, 2)methanol, 45 min, reflux 3: 60 percent / NaOH / methanol; H2O / 1) 12 h, r. t., 2) 6 h, reflux 4: 0.1 N (CH3)3CONa / diethyl ether; 2-methyl-propan-2-ol / 20 h / Ambient temperature 5: 61 percent / 10percent H2SO4 / methanol / 24 h / Ambient temperature 7: 77 percent / conc. HCl / pyridine / 1 h / 210 °C View Scheme

1: 1) KOH, hydroquinone / 1) ethanol,H2O, 16 h, reflux, 2) ether 2: 1) Na / 1) methanol, 30 min, 60 deg C, 2)methanol, 45 min, reflux 3: 60 percent / NaOH / methanol; H2O / 1) 12 h, r. t., 2) 6 h, reflux 4: 0.1 N (CH3)3CONa / diethyl ether; 2-methyl-propan-2-ol / 20 h / Ambient temperature 5: 61 percent / 10percent H2SO4 / methanol / 24 h / Ambient temperature 6: 1) mesitol, molecular sieve, 2) K, aniline / 1) pyridine, anh. methylcyclohexane, 10 h, irradiation, 2) liq. NH3 View Scheme

1: 1) KOH, hydroquinone / 1) ethanol,H2O, 16 h, reflux, 2) ether 2: 1) Na / 1) methanol, 30 min, 60 deg C, 2)methanol, 45 min, reflux 3: 60 percent / NaOH / methanol; H2O / 1) 12 h, r. t., 2) 6 h, reflux 4: 0.1 N (CH3)3CONa / diethyl ether; 2-methyl-propan-2-ol / 20 h / Ambient temperature 5: 61 percent / 10percent H2SO4 / methanol / 24 h / Ambient temperature View Scheme

1: KOH, hydroquinone / ethanol / 16 h / Heating 2: diethyl ether 5: 89 percent / hydrogen / Lindlar-catalyst / petroleum ether / Ambient temperature View Scheme