sulfuric acid in benzene 4 h; Heating;

sulfuric acid

in methanol

1.1: POCl3; Et3N / diethyl ether / 1.25 h / -5 - 20 °C 2.1: Et3N / diethyl ether / -20 - 20 °C 3.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -50 - 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -50 °C 4.2: 74 percent / tetrahydrofuran; hexane / 1 h / -50 - 20 °C 5.1: 61 percent / aq. H2SO4 / benzene / 4 h / Heating View Scheme

1.1: Et3N / diethyl ether / -20 - 20 °C 2.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -50 - 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -50 °C 3.2: 74 percent / tetrahydrofuran; hexane / 1 h / -50 - 20 °C 4.1: 61 percent / aq. H2SO4 / benzene / 4 h / Heating View Scheme

1.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -50 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -50 °C 2.2: 74 percent / tetrahydrofuran; hexane / 1 h / -50 - 20 °C 3.1: 61 percent / aq. H2SO4 / benzene / 4 h / Heating View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -50 °C 1.2: 74 percent / tetrahydrofuran; hexane / 1 h / -50 - 20 °C 2.1: 61 percent / aq. H2SO4 / benzene / 4 h / Heating View Scheme

in methanol

(i) Mg, EtOH, CCl4, Et2O, (ii) /BRN= 471389/, (iii) TsOH, toluene; Multistep reaction;

1: 65 percent / 84 h / Ambient temperature 2: 8 percent / LiAlH4 / tetrahydrofuran / 2.75 h / 35 °C View Scheme