methanesulfonic acid T=100°C; 1.5 h;

potassium hydroxide; oxygen in ethanol 3 h;

sodium dichromate in acetic acid 0.416667 h; Heating;

lithium diisopropyl amide in tetrahydrofuran; hexane T=-40 - 25°C; 2 h;

chloranil; trichloroacetic acid in toluene T=105°C; 288 h;

N-bromosuccinmide in water; dimethyl sulfoxide 30 h;

1: 94 percent / NaBH4, O2 / ethanol / 72 h 2: N-bromosuccinimide / dimethylsulfoxide; H2O / 30 h View Scheme

1: 1.) Mg, I2 / 1.) THF, reflux, 30 min, 2.) THF, reflux, 2 h 2: 50 percent / sulfuric acid, H2O / 1.5 h / 100 °C 3: 99 percent / benzene; diethyl ether / 16 h / Heating 4: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating 5: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h 6: 94 percent / NaBH4, O2 / ethanol / 72 h 7: N-bromosuccinimide / dimethylsulfoxide; H2O / 30 h View Scheme

1: 99 percent / benzene; diethyl ether / 16 h / Heating 2: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h 4: 94 percent / NaBH4, O2 / ethanol / 72 h 5: N-bromosuccinimide / dimethylsulfoxide; H2O / 30 h View Scheme

1: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h 2: 94 percent / NaBH4, O2 / ethanol / 72 h 3: N-bromosuccinimide / dimethylsulfoxide; H2O / 30 h View Scheme