in isopropyl alcohol T=5 - 20°C; Heating / reflux; Product distribution / selectivity;

in water; acetone T=25 - 58°C; 0.5 h;

1.1: sodium methylate / methanol / 3 h / -5 - 0 °C 1.2: 49 h / -5 °C 2.1: hydrogen; acetic acid / palladium on carbon / 4 h / 43 - 47 °C / 8606.2 Torr 3.1: formic acid / 53 - 57 °C 4.1: sodium methylate; lauryl mercaptan / polyethylene glycol (PEG-400); methanol / 145 - 150 °C 4.2: 4 h / 105 - 115 °C 4.3: 2 h / 5 - 30 °C 5.1: water; acetone / 6 h / 10 - 30 °C / Reflux View Scheme

1.1: sodium methylate / methanol / 3 h / -5 - 0 °C 1.2: 49 h / -5 °C 2.1: hydrogen; acetic acid / palladium on carbon / 4 h / 43 - 47 °C / 8606.2 Torr 3.1: formic acid / 53 - 57 °C 4.1: sodium methylate; lauryl mercaptan / polyethylene glycol (PEG-400); methanol / 145 - 150 °C 4.2: 4 h / 105 - 115 °C 4.3: 2 h / 5 - 30 °C 5.1: water; acetone / 6 h / 10 - 30 °C / Reflux View Scheme

1.1: sodium hydroxide / water / pH 12 - 13 2.1: benzenethiol sodium salt / N,N-dimethyl-formamide / 150 - 160 °C 2.2: 0.5 h / 25 - 35 °C / pH 3.5 3.1: water; acetone / 57 - 63 °C / Inert atmosphere View Scheme

1.1: benzenethiol sodium salt / N,N-dimethyl-formamide / 150 - 160 °C 1.2: 0.5 h / 25 - 35 °C / pH 3.5 2.1: water; acetone / 57 - 63 °C / Inert atmosphere View Scheme