1: 9.5 g / K2CO3 / acetone / 3 h / Heating 2: LiCl / H2O; dimethylsulfoxide / 2 h / 165 °C 3: LiAlH4 / diethyl ether / 2 h / Heating 4: MnO2 / benzene / 12 h / Heating View Scheme

1.1: acetic acid; bromine / 20.25 h / 20 °C / |Cooling with ice 2.1: potassium carbonate / acetone / 15 h / 30 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 3.2: 2 h / |Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 5.2: 10 h / -78 - -30 °C / |Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 7.1: acetic anhydride; sodium acetate / 2 h / |Reflux 8.1: sodium hydroxide / methanol; water / |Reflux 9.1: potassium carbonate / acetone / 12 h / 20 °C 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 10.2: 10 h / 20 °C 11.1: silver(l) oxide / methanol / 3 h / 20 °C 12.1: potassium carbonate / acetone / 5 h / 20 °C 13.1: dichloromethane / 0.5 h / 20 °C 14.1: lithium hydroxide hydrate / water; tetrahydrofuran / 1 h / 20 °C 15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / |Inert atmosphere View Scheme