1: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h View Scheme

1: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h 3: 94 percent / NaBH4, O2 / ethanol / 72 h 4: m-chlorobenzoic acid / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h 3: 94 percent / NaBH4, O2 / ethanol / 72 h View Scheme

lithium aluminium tetrahydride; titanium(III) chloride in tetrahydrofuran 2 h; Heating; Yield given;

1: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h 3: 94 percent / NaBH4, O2 / ethanol / 72 h 4: N-bromosuccinimide / dimethylsulfoxide; H2O / 30 h View Scheme