1: 1.) triethylamine; 2.) 20percent HCl / 1.) chloroform, 35 deg C, 5 h; 2.) chloroform, reflux, 5 h 2: sodium hydroxide / ethanol / 1 h / Heating 3: 1.) hydrazine hydrate; 2.) potassium hydroxide / 1.) triethanolamine, 130 deg C; reflux, 4 h; 2.) triethanolamine, 200 deg C, 9 h 4: thionyl chloride / 1 h / 50 °C 5: 1.) triethylamine; 2.) 20percent HCl / 1.) chloroform, 35 deg C, 5 h; 2.) chloroform, reflux, 5 h 6: sodium hydroxide / ethanol / 1 h / Heating 7: 1.) hydrazine hydrate; 2.) potassium hydroxide / 1.) triethanolamine, 130 deg C; reflux, 4 h; 2.) triethanolamine, 200 deg C, 9 h 8: thionyl chloride / 1 h / 50 °C View Scheme

1: methylmagnesium bromide With tributylphosphine in tetrahydrofuran T=20°C; 0.333333 h; 2: hexane-1,6-dicarboxylic acid dichloride in tetrahydrofuran T=-40°C; 0.333333 h;

toluene

in benzene Heating;

1: diethyl ether 2: 39.5 g / HBr / diethyl ether View Scheme

1: diethyl ether 2: aq. HCl, NaCl / methanol View Scheme

diethyl ether Beim Behandeln des erhaltenen 1.6-Bis-diazoacetyl-hexans mit HCl in Aether+Chloroform;

1: bromine / 14 h / 80 °C 2: 20 °C / Cooling with ice; Reflux 3: 1,3,5-trishydroxybenzene; sodium nitrite / N,N-dimethyl-formamide / 2.5 h / 20 °C View Scheme

in diethyl ether T=-35°C; 1 h;

1: 59 percent / -196 deg C to 40 deg C 2: 80.8 percent / tetrahydrofuran / 0.5 h View Scheme