1.1: 99 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 2.1: 93 percent / thionyl chloride / CHCl3 / 0 - 20 °C 3.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 3.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 4.1: potassium hydroxide / H2O / 5 h / Heating 4.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 5.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 6.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 7.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 8.1: ozone / methanol; CH2Cl2 / -78 °C 8.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 9.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 10.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 10.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 10.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 11.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 12.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

sodium methylate in N,N-dimethyl-formamide 13 h; Ambient temperature;

sodium methylate in N,N-dimethyl-formamide

1: benzene / 3.5 h / Heating 2: 13.3 percent / cc H2SO4, P2O5 / 0.75 h / 155 °C 3: 7.5 percent / K2CO3, Cu, iodine / neat (no solvent) / 24 h / 120 °C / pression flask 4: hydrazin hydrate / Raney Ni / aq. ethanol / 1 h / 100 °C 5: NaNO2 / acetic acid; H2O / 1 h / 0 °C 6: 3 percent / methanol / 500 °C / in Vigreux column View Scheme