toluene-4-sulfonic acid in methanol

in P2O5

toluene-4-sulfonic acid

1: 41 percent / ethanol; diethyl ether / 72 h / -2 °C 2: 72 percent / dimethylsulfoxide / 3 h / 50 °C 3: 30percent aq.H2SO4 / aq. acetic acid / 16 h / Heating 4: 58 g / p-toluenesulfonic acid / benzene / 6 h / Heating View Scheme

1: 72 percent / dimethylsulfoxide / 3 h / 50 °C 2: 30percent aq.H2SO4 / aq. acetic acid / 16 h / Heating 3: 58 g / p-toluenesulfonic acid / benzene / 6 h / Heating View Scheme

1: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 2: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 3: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 4: 9.8 g / pyridine 5: 7.8 g / NaOH/85percent aq. MeOH / 2.5 h / Heating 6: 6.2 g / Jones' reagent / acetone / 0.5 h / 0 - 5 °C 7: 0.18 g / diethyl ether View Scheme

1: 1.) H2SO4, H2O2 (28percent w/v), 2.) NaOH / 1.) 40 deg C, 8 h, 2.) MeOH, water, reflux, 5 h 2: 52.5 g / 5percent methanolic HCl / 48 h / Ambient temperature 3: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C 4: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 5: 40 g / 10percent aq. NaOH / 4 h / Heating 6: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 7: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 8: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 9: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 10: 9.8 g / pyridine 11: 7.8 g / NaOH/85percent aq. MeOH / 2.5 h / Heating 12: 6.2 g / Jones' reagent / acetone / 0.5 h / 0 - 5 °C 13: 0.18 g / diethyl ether View Scheme

1: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 2: 40 g / 10percent aq. NaOH / 4 h / Heating 3: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 4: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 5: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 6: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 7: 9.8 g / pyridine 8: 7.8 g / NaOH/85percent aq. MeOH / 2.5 h / Heating 9: 6.2 g / Jones' reagent / acetone / 0.5 h / 0 - 5 °C 10: 0.18 g / diethyl ether View Scheme

1: 52.5 g / 5percent methanolic HCl / 48 h / Ambient temperature 2: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C 3: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 4: 40 g / 10percent aq. NaOH / 4 h / Heating 5: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 6: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 7: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 8: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 9: 9.8 g / pyridine 10: 7.8 g / NaOH/85percent aq. MeOH / 2.5 h / Heating 11: 6.2 g / Jones' reagent / acetone / 0.5 h / 0 - 5 °C 12: 0.18 g / diethyl ether View Scheme

1: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C 2: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 3: 40 g / 10percent aq. NaOH / 4 h / Heating 4: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 5: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 6: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 7: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 8: 9.8 g / pyridine 9: 7.8 g / NaOH/85percent aq. MeOH / 2.5 h / Heating 10: 6.2 g / Jones' reagent / acetone / 0.5 h / 0 - 5 °C 11: 0.18 g / diethyl ether View Scheme