phenyl-phosphonic acid in benzene 24 h;

toluene-4-sulfonic acid in benzene 72 h; Heating; Title compound not separated from byproducts;

1: H+ / toluene 2: 72.5 percent / magnesium sulfate, potassium permanganate / H2O / 0.5 h / 6 °C 3: 63 percent / pyridine, methanesulfonyl chloride / 1.) RT, overnight, 2.) reflux, 4 h View Scheme

1: 72.5 percent / magnesium sulfate, potassium permanganate / H2O / 0.5 h / 6 °C 2: 63 percent / pyridine, methanesulfonyl chloride / 1.) RT, overnight, 2.) reflux, 4 h View Scheme

toluene-4-sulfonic acid; ethylene glycol; benzene

1: 95.2 percent / NaNH2, Fe(NO3)3 / liquid ammonia; toluene / reflux, 2 h then R.T. overnight 2: 2.) 10percent KOH, 3.) Amberlyst A-15 / 1.) Pd<P(C6H5)3>4, 2.) tetrabutylammonium hydrogen sulfate / 1.) 4.5 h, 2.) reflux, 4 h, 3.) acetone, R.T., 18 h 3: 92.4 percent / p-toluenesulfonic acid / toluene / 20 h / Heating View Scheme

1: 80 percent / Li / tetrahydrofuran / 1.) 10-15 deg C, 2.) r.t., 1 h 2: 80 percent / PBr3, pyridine / toluene / 1 h / -10 °C 3: 1.) DBU, 2.) 1 M aq. HCl / 1.) toluene, reflux, 5 h, 2.) THF, 25 deg C, 5 h View Scheme

1: 82 percent / Li / tetrahydrofuran / 5 h / Ambient temperature 2: 0.1 N HCl / tetrahydrofuran / 20 h / Ambient temperature 3: 0.1 N H2SO4 / CH2Cl2 / 0.5 h View Scheme

1: 1.) Mg, EtBr / 1.) THF, r.t., 1 h, 2.) THF, reflux, 15 h 2: 99 percent / H2, KOH / Pd/Al2O3 / ethanol 3: 67 percent / 5percent HCl / acetone / 15 h 4: 30 percent / H2 / PtO2 / acetic acid 5: 80 percent / pyridine / tetrahydrofuran / 15 h View Scheme

(i) Li, Fe(NO3)3, liq. NH3, (ii) /BRN= 157441/, Et2O, (iii) LiAlH4, THF; Multistep reaction;