toluene-4-sulfonic acid in benzene

sodium acetate; pyridinium chlorochromate in dichloromethane 4 h;

T=120°C; P=20 Torr; 0.25 h;

nickel in dimethyl sulfoxide

1: 28.1 g / tetrabutylammonium hydrogenosulfate; phosphate buffer / H2O / 5 h / 60 °C / pH 7.8 2: 18.0 g / HCl / H2O / 70 °C / pH 1 View Scheme

1: KOH / H2O / 20 °C 2: 28.1 g / tetrabutylammonium hydrogenosulfate; phosphate buffer / H2O / 5 h / 60 °C / pH 7.8 3: 18.0 g / HCl / H2O / 70 °C / pH 1 View Scheme

1: 1.) n-butyl-lithium, TMEDA 2.) n-butyl-lithium / 1.) hexane, THF, 0 deg C, 15 min 2.) 30 min, hexane, THF 2: 49 percent / toluene-p-sulphonic acid / benzene / 0.02 h 3: 100 percent / sodium periodate / H2O; methanol / 18 h / Ambient temperature 4: 56 percent / 0.25 h / 120 °C / 20 Torr View Scheme

1: 100 percent / sodium periodate / H2O; methanol / 18 h / Ambient temperature 2: 56 percent / 0.25 h / 120 °C / 20 Torr View Scheme

1: 49 percent / toluene-p-sulphonic acid / benzene / 0.02 h 2: 100 percent / sodium periodate / H2O; methanol / 18 h / Ambient temperature 3: 56 percent / 0.25 h / 120 °C / 20 Torr View Scheme

1: 1.) n-butyl-lithium / 1.) hexane, THF, 0 deg C, 15 min 2.) 1 h, hexane, THF 2: 1.) n-butyl-lithium, TMEDA 2.) n-butyl-lithium / 1.) hexane, THF, 0 deg C, 15 min 2.) 30 min, hexane, THF 3: 49 percent / toluene-p-sulphonic acid / benzene / 0.02 h 4: 100 percent / sodium periodate / H2O; methanol / 18 h / Ambient temperature 5: 56 percent / 0.25 h / 120 °C / 20 Torr View Scheme