1: 58 percent / tetrahydrofuran / 8 h / Heating 2: 93 percent / acetic acid / Ambient temperature 3: 71 percent / acetic acid, sodium triacetoxyborohydride / 1,2-dichloro-ethane View Scheme

1: 58 percent / tetrahydrofuran / 8 h / Heating 2: 93 percent / acetic acid / Ambient temperature 3: 71 percent / acetic acid, sodium triacetoxyborohydride / 1,2-dichloro-ethane 4: 82.5 percent / potassium hydroxide / various solvent(s) / 4 h / 57 °C / solvent: N-methyl-pyrrolidinone 5: aq. HCl 6: 94 percent / thionyl chloride / 3 h / Heating 7: 1.) sodium hydrosulfite, 2.) aq. HCl / 1.) THF, ethanol, water, steam bath, 4 h, 2.) THF, ethanol, 15 min, steam bath View Scheme

1: 58 percent / tetrahydrofuran / 8 h / Heating 2: 93 percent / acetic acid / Ambient temperature 3: 71 percent / acetic acid, sodium triacetoxyborohydride / 1,2-dichloro-ethane 4: 82.5 percent / potassium hydroxide / various solvent(s) / 4 h / 57 °C / solvent: N-methyl-pyrrolidinone 5: aq. HCl 6: 94 percent / thionyl chloride / 3 h / Heating 7: 1.) sodium hydrosulfite, 2.) aq. HCl / 1.) THF, ethanol, water, steam bath, 4 h, 2.) THF, ethanol, 15 min, steam bath View Scheme

sulfuric acid; nitric acid in acetic acid 2 h; Ambient temperature;

1: in N,N-dimethyl-formamide T=20°C; Alkylation; 2: With dimethyl sulfoxide; sodium chloride T=160 - 170°C; Decarboxylation; Krapcho's reaction; 12 h;

sulfuric acid; nitric acid T=-5 - 0°C; Diazotieren und nachfolgend Behandeln mit Kupfer(I)-chlorid in Salzsaeure bei 70grad;

1: HNO3+H2SO4 / 40 - 45 °C / dann bei 90grad 2: alcohol; ammonia 3: Diazotization.folgend Behandeln mit Kupfer(I)-chlorid in Salzsaeure View Scheme

1: HNO3+H2SO4 / 8 - 10 °C / man trennt die Isomeren durch aufeinanderfolgende fraktionierte Krystallisation aus konz. Schwefelsaeure und Alkohol 2: alcohol; ammonia 3: Diazotization.folgend Behandeln mit Kupfer(I)-chlorid in Salzsaeure View Scheme

1: alcohol; ammonia 2: Diazotization.folgend Behandeln mit Kupfer(I)-chlorid in Salzsaeure View Scheme

iodine; chlorine; iron in dichloromethane T=25°C; var. temp., var. time; Product distribution;