1: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, 0 deg C, 10 min; room temperature, 30 min 2: 80 percent / benzene / 15 h / Ambient temperature 3: 1) Ti(Oi-Pr)4, diethyl L-(+)-tartrate, tert-butyl hydroperoxide, 4 Angstroem molecular sieves / 1) CH2Cl2, -20 deg C, 20 h, 2) CH2Cl2, hexane, room temperature, 16 h 4: NaIO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 5: 4.34 g / CBr4, PPh3 / CH2Cl2 / 0.33 h / 0 °C 6: 87 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C View Scheme

1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-60°C; 1.5 h; Inert atmosphere; 2: With triethylamine in dichloromethane T=-60 - 20°C; Inert atmosphere;

potassium hydroxide in dimethyl sulfoxide T=20°C; 2.5 h;

1: Trimethylene glycol With sodium hydride in tetrahydrofuran T=0°C; 1 h; Inert atmosphere; 2: 1-bromomethyl-4-methoxy-benzene With tetra-(n-butyl)ammonium iodide in tetrahydrofuran T=20°C; 4 h; Inert atmosphere;

diisobutylaluminium hydride in diethyl ether; hexane T=0°C; 1 h;

Amberlyst-15 in dichloromethane 4 h; Reflux; regioselective reaction;

sodium perchlorate monohydrate; water; sodium hydrogencarbonate in acetonitrile T=20°C; Electrolysis; chemoselective reaction;

1: Trimethylene glycol With sodium hydride in N,N-dimethyl-formamide T=0°C; 0.5 h; 2: 1-(chloromethoxymethyl)-4-methoxybenzene in N,N-dimethyl-formamide T=0°C; 2.33333 h;

1: amberlyst 15; magnesium sulfate / CH2Cl2 2: diisobutylaluminum hydride / CH2Cl2 / 0 °C View Scheme

trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex in dichloromethane