toluene-4-sulfonic acid in benzene 7 h; Heating;

1.1: 90 percent / PTSA / benzene / 7 h / Heating 2.1: n-BuLi / diethyl ether; hexane / -70 °C 2.2: 64 percent / diethyl ether; hexane / 1 h / -70 - 20 °C 3.1: 92 percent / HCl / H2O; diethyl ether / 1 h / 20 °C 4.1: methanol / 1 h / 20 °C 4.2: 80 percent / sodium borohydride; methanol / 1 h / 0 °C 5.1: 74 percent / benzene / 2 h / Heating View Scheme

sodium tetrahydroborate in methanol; water

1.1: 90 percent / PTSA / benzene / 7 h / Heating 2.1: n-BuLi / diethyl ether; hexane / -70 °C 2.2: 64 percent / diethyl ether; hexane / 1 h / -70 - 20 °C 3.1: 92 percent / HCl / H2O; diethyl ether / 1 h / 20 °C View Scheme

1: 79 percent / 20percent aq. NaOH, NaBH4 / methanol / 0.25 h / 0 °C 2: CH3OD / tetrahydrofuran / 18 h 3: 1.) n-BuLi, 2.) MeOH / multistep reaction; mechanism of halogen-lithium exchange intramolecularly competitve with removal of an acidic hydrogen View Scheme

1.1: 90 percent / PTSA / benzene / 7 h / Heating 2.1: n-BuLi / diethyl ether; hexane / -70 °C 2.2: 64 percent / diethyl ether; hexane / 1 h / -70 - 20 °C 3.1: 92 percent / HCl / H2O; diethyl ether / 1 h / 20 °C 4.1: methanol / 1 h / 20 °C 4.2: 80 percent / sodium borohydride; methanol / 1 h / 0 °C 5.1: 74 percent / benzene / 2 h / Heating View Scheme

hydrogenchloride; sodium iodide in acetonitrile Heating;

1: 90 percent / POCl3 2: NaI, HCl / acetonitrile View Scheme