hydrogenchloride 1.) benzene, 18 h, 23 deg C 2.) benzene, 0 deg C, 30 min; Yield given. Multistep reaction;

1: 53.1 percent / sodium carbonate / xylene / 5 h / Heating 2: 1) ozone; 2) p-toluenesulfonic acid / 1) MeOH, 2 h, -70 deg C; 2) MeOH, RT View Scheme

toluene-4-sulfonic acid; ozone 1) MeOH, 2 h, -70 deg C; 2) MeOH, RT; Yield given. Multistep reaction;

1: 88 percent / BH3.THF / 10 molepercent (S)-oxazaborolidine / tetrahydrofuran / 0.03 h / 10 °C 2: 91 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 12 h / 23 °C 3: 87 percent / cuprous cyanide / diethyl ether / 2 h / -20 °C 4: 1.) 1.5 eq. BH3*THF, 2.) alkaline hydrogen peroxide / 1.) 0 deg C, 1 h.; 23 deg C 1 h. 5: 79 percent / 1.2 eq. pyridinium dichromate / CH2Cl2 / 2 h / 0 °C / 4A mol. sieves View Scheme