hydrogenchloride in methanol; benzene 0.5 h; Ambient temperature;

potassium tert-butylate in tert-butyl alcohol 0.5 h; Heating;

1: 68 percent / N-bromosuccinimide / 2 h / Ambient temperature 2: 74 percent / KO-t-Bu / 2-methyl-propan-2-ol / 0.5 h / Heating View Scheme

triethylamine

1: aq. HClO4 2: Et3N View Scheme

1: (i) O2, (ii) KI, aq. AcOH 2: aq. HClO4 3: Et3N View Scheme

1: 1.) O3, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, RT, 12 h 2: 1.) KH / 1.) THF, RT, 2.) THF, from -78 deg C to RT 3: 83 percent / aq. NaOH / 48 h View Scheme

n-butyllithium in tetrahydrofuran; hexane T=-78°C; 4 h;

1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -78 °C 2: hydrogen chloride / 1 h / Ambient temperature View Scheme

1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -78 °C 2: hydrogen chloride / 1 h / Ambient temperature 3: 99 percent / hydrogen chloride / methanol; benzene / 0.5 h / Ambient temperature 4: 40.5 percent / xylene / 6 h / Heating 5: 50 percent / bis(triphenylphosphine)nickel dicarbonyl / bis-(2-methoxy-ethyl) ether / 12 h / Heating 6: 98 percent / lithium aluminum hydride / diethyl ether / 0.33 h / Ambient temperature 7: 81 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme