1: aq. KOH / ethanol / Heating 2: Heating View Scheme

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: 76 percent / N2H4*H2O, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 125 deg C, 6 h; 195 deg C, 3 h View Scheme

1: n-butyl-malonic acid diethyl ester With ethanol; sodium Metallation; 2: methyl iodide in tetrahydrofuran T=20°C; Methylation; 2 h;

hydrogen; palladium on activated charcoal in ethanol; triethylamine

1: methyl malonic acid diethylester With sodium in ethanol Heating; 2: 1-bromo-butane in ethanol Heating;

Yield given. Multistep reaction. Yields of byproduct given;

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

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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 View Scheme