toluene-4-sulfonic acid in benzene

1: diethyl ether 2: conc. HCl / 48 h / Ambient temperature View Scheme

1: BH3*Me2S / tetrahydrofuran / 2 h / 0 - 23 °C 2: pyridine; CH2Cl2 / 6 h / 24 °C 3: NaOMe / 0.33 h 4: 79 percent / n-BuLi, CuCN / diethyl ether / -70 - -50 °C 5: DIBAL-H / toluene / 3 h / -78 °C 6: toluene / 15 h / 23 °C 7: DMAP, Et3N / pyridine / 26 h / 45 °C 8: DIBAL-H / toluene / 1 h / -78 °C 9: CBr4, PPh3 / CH2Cl2 / 1 h 10: Ph3P / acetonitrile / 6 h 11: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h 12: 90 percent / n-Bu4NF / tetrahydrofuran / 12 h 13: LiOH / tetrahydrofuran; H2O View Scheme

1: SOCl2 / 4 h / Heating 2: H2 / 5percent Pd/BaSO4 / toluene / 20 h / 50 °C View Scheme

1: 83 percent / 2N borane dimethylsulfide / tetrahydrofuran / 15 h / 0 °C 2: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH2Cl2 / 3.5 h / Ambient temperature 3: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane 4: 30percent H2O2 / 0 °C View Scheme

toluene-4-sulfonic acid in benzene

1: diethyl ether 2: conc. HCl / 48 h / Ambient temperature View Scheme

sulfuric acid T=20°C; 48 h;

thionyl chloride

oxalyl dichloride in benzene 1.) 1 h, 50 deg C; 2.) 24 h, r.t.;