in benzene 2 h; Heating;

1.1: 90 percent / PTSA / benzene / 7 h / Heating 2.1: n-BuLi / diethyl ether; hexane / -70 °C 2.2: 64 percent / diethyl ether; hexane / 1 h / -70 - 20 °C 3.1: 92 percent / HCl / H2O; diethyl ether / 1 h / 20 °C 4.1: methanol / 1 h / 20 °C 4.2: 80 percent / sodium borohydride; methanol / 1 h / 0 °C 5.1: 74 percent / benzene / 2 h / Heating View Scheme

1.1: 92 percent / HCl / H2O; diethyl ether / 1 h / 20 °C 2.1: methanol / 1 h / 20 °C 2.2: 80 percent / sodium borohydride; methanol / 1 h / 0 °C 3.1: 74 percent / benzene / 2 h / Heating View Scheme

1.1: n-BuLi / diethyl ether; hexane / -70 °C 1.2: 64 percent / diethyl ether; hexane / 1 h / -70 - 20 °C 2.1: 92 percent / HCl / H2O; diethyl ether / 1 h / 20 °C 3.1: methanol / 1 h / 20 °C 3.2: 80 percent / sodium borohydride; methanol / 1 h / 0 °C 4.1: 74 percent / benzene / 2 h / Heating View Scheme

1: 92 percent / aq. HCl / 4 h / Heating 2: 88 percent View Scheme

1.1: methanol / 1 h / 20 °C 1.2: 80 percent / sodium borohydride; methanol / 1 h / 0 °C 2.1: 74 percent / benzene / 2 h / Heating View Scheme

(i), (ii) aq. HBr; Multistep reaction;

Hydrolysis; Alkaline hydrolysis;

1: 83 percent / Alkaline hydrolysis 2: 40 percent / pyridine / acetonitrile / 12 h / 20 °C 3: 40 percent / sodium acetate / acetic acid / 20 h / 20 °C 4: 68 percent / sodium acetate; hydrogen / Pd(OH)2/C / ethanol / 24 h / 20 °C 5: 66 percent / NaOMe / methanol / 10 h / 20 °C 6: 60 percent / PCC; celite / CH2Cl2 / 12 h / 20 °C View Scheme