1: 86 percent / lithium chloride / H2O; dimethylsulfoxide / 6 h / Heating 2: 100 percent / LiAlH4 / tetrahydrofuran / 0.75 h / 0 °C View Scheme

1: KOH / ethanol 2: 175 °C 3: 87 percent / LiAlH4 / diethyl ether / Heating 4: 74 percent / Ph3PBr2 / CH2Cl2 / 0 - 10 °C View Scheme

lithium chloride in water; dimethyl sulfoxide 6 h; Heating;

1: aqu. KOH / ethanol / 5 h / Heating 2: 1.) 30 min, 150 deg; 2.) in 15 min to 180 deg C 3: H2SO4 / 1 h / Heating 4: 1.) LiAlH4; 2.) HCl / 1.) diethyl ether, 8 h, reflux; 2.) 0 deg C, water 5: pyridine / 1 h / 0 °C 6: LiBr / acetone / 5 h / Heating 8: KOH / ethanol; H2O / 5 h / Heating 9: 83 percent / N2H4*H2O, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 125 deg C, 6 h; 195 deg C, 3 h View Scheme

1: methyl malonic acid diethylester With sodium hydride in tetrahydrofuran 2: 1-bromo-octane in tetrahydrofuran 20 h; Heating / reflux;

1: methyl malonic acid diethylester With sodium hydride in N,N-dimethyl-formamide T=0°C; 0.5 h; 2: 1-iodo-n-octane in N,N-dimethyl-formamide T=0 - 20°C;

sodium hydride 1.) toluene, 1 h - room temperature, 10 h - reflux; 2.) 10 h, reflux; Multistep reaction;

ethanol

1: 86 percent / lithium chloride / H2O; dimethylsulfoxide / 6 h / Heating 2: 100 percent / LiAlH4 / tetrahydrofuran / 0.75 h / 0 °C 3: 100 percent / triethylamine; SO3*pyridine; DMSO / CH2Cl2 / 0 - 20 °C View Scheme

1: KOH / ethanol 2: 175 °C View Scheme