1: 1.) n-BuLi / 1.) THF, RT, 2 h, 2.) THF, 4 h 2: 96 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 3 h / Heating 3: 1.) NaH / 1.) THF, 0 deg C, 2.) THF, from 55 deg C to 60 deg C, 5 h 4: 1.) aq. NaOH, 2.) 2N H2SO4 / 1.) EtOH, reflux, 8 h, 2.) reflux, 4 h View Scheme

1: 1.) aq. KOH, 2.) quinoline / 1.) EtOH, reflux, 12h, 2.) reflux, 2 h 2: 1.) n-BuLi / 1.) THF, RT, 2 h, 2.) THF, 4 h 3: 96 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 3 h / Heating 4: 1.) NaH / 1.) THF, 0 deg C, 2.) THF, from 55 deg C to 60 deg C, 5 h 5: 1.) aq. NaOH, 2.) 2N H2SO4 / 1.) EtOH, reflux, 8 h, 2.) reflux, 4 h View Scheme

1: 74 percent / conc. H2SO4 / ethanol / 8 h / Heating 2: 1.) aq. KOH, 2.) quinoline / 1.) EtOH, reflux, 12h, 2.) reflux, 2 h 3: 1.) n-BuLi / 1.) THF, RT, 2 h, 2.) THF, 4 h 4: 96 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 3 h / Heating 5: 1.) NaH / 1.) THF, 0 deg C, 2.) THF, from 55 deg C to 60 deg C, 5 h 6: 1.) aq. NaOH, 2.) 2N H2SO4 / 1.) EtOH, reflux, 8 h, 2.) reflux, 4 h View Scheme

1: 96 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 3 h / Heating 2: 1.) NaH / 1.) THF, 0 deg C, 2.) THF, from 55 deg C to 60 deg C, 5 h 3: 1.) aq. NaOH, 2.) 2N H2SO4 / 1.) EtOH, reflux, 8 h, 2.) reflux, 4 h View Scheme

1: 73 percent / Na2CO3 / CH2Cl2 / 24 h / Ambient temperature 2: 74 percent / zinc / acetic acid / 24 h / Ambient temperature 3: 98 percent / 1 M aq. NaOH / methanol / 15 h / Ambient temperature View Scheme

1: 74 percent / zinc / acetic acid / 24 h / Ambient temperature 2: 98 percent / 1 M aq. NaOH / methanol / 15 h / Ambient temperature View Scheme

sodium hydroxide; sulfuric acid 1.) EtOH, reflux, 8 h, 2.) reflux, 4 h; Yield given. Multistep reaction;

1: 1.) NaH / 1.) THF, 0 deg C, 2.) THF, from 55 deg C to 60 deg C, 5 h 2: 1.) aq. NaOH, 2.) 2N H2SO4 / 1.) EtOH, reflux, 8 h, 2.) reflux, 4 h View Scheme

sodium hydroxide anschliessend Erhitzen des Reaktionsgemisches mit Essigsaeure;

1: NaOH; toluene 2: aq.-ethanolic NaOH / anschliessend Erhitzen des Reaktionsgemisches mit Essigsaeure View Scheme