1: pyridinium chlorochromate / dichloromethane / 20 °C 2: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme

(i) NaBH4, aq. KOH, (ii) /BRN= 1098229/, HCl; Multistep reaction;

1: benzene; pyridine 2: acetic acid; chlorobenzene; chromium (VI)-oxide / weiteres Reagens: Wasser; anschliessend Behandeln mit Schwefelsaeure 4: ethanolic sodium ethylate / 170 - 200 °C View Scheme

1: With water; lithium hydroxide hydrate in tetrahydrofuran T=20°C; 2: With ammonium chloride in tetrahydrofuran; water; ethyl acetate

1: benzene; pyridine 2: acetic acid; chlorobenzene; chromium (VI)-oxide / weiteres Reagens: Wasser; anschliessend Behandeln mit Schwefelsaeure 3: chlorobenzene; acetic acid; selenium dioxide / weiteres Reagens: Chlorwasserstoff; Behandeln des Reaktionsprodukts mit methanol. Natronlauge 4: methanol; aqueous hydrochloric acid View Scheme

1: (i) MeSO2Cl, Py, (ii) LiAlH4 2: (i) MeSO2Cl, Py, (ii) LiAlH4 3: CrO3, aq. AcOH 4: LiAlH4 / diethyl ether / Heating 5: Py 6: LiAlH4 / diethyl ether / Heating View Scheme

1: AgCO3-Celite / toluene 2: 9 g / N,N-dimethylaminopyridine, Et3N / CH2Cl2 / 0.5 h 3: 138 mg / Br2 / acetic acid / 1 h / Ambient temperature 4: 62 mg / Cr(OAc)2 / CHCl3; acetic acid / 1 h / Ambient temperature 5: 26 mg / Li2CO3, LiBr / dimethylformamide / 4 h / 80 °C 6: 30 percent H2O2, 2 N NaOH / dioxane / 24 h / Ambient temperature 7: diethyl ether 8: 58 mg / Cr(OAc)2 / ethanol / 1 h / Ambient temperature 9: 15 mg / NaBH4 / propan-2-ol / 0.5 h 10: 178 mg / 2 N LiOH / methanol / 1 h / Heating View Scheme

1: (i) Et2O, benzene, (ii) /BRN= 385737/, AcOH 2: (i) NBS, CCl4, (ii) KI, acetone View Scheme

1: benzene 2: pyridine / 100 °C / Kochen des Reaktionsprodukts mit Eisessig View Scheme

(i) Et2O, benzene, (ii) /BRN= 385737/, AcOH; Multistep reaction;