1: 6-hydroxymethyl-1,4-dioxaspiro[4,4]nonane With sodium hydride in tetrahydrofuran T=20°C; 0.5 h; 2: benzyl bromide in tetrahydrofuran 28 h; Heating;

tetra-(n-butyl)ammonium iodide in tetrahydrofuran; hexane; ethyl acetate

1.1: 83 percent / LiAlH4 / diethyl ether / 1.5 h / Heating 2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C 2.2: 69 percent / tetrahydrofuran / 28 h / Heating View Scheme

1.1: 98 percent / p-TsOH*H2O / CH2Cl2 / 24 h / Heating 2.1: 83 percent / LiAlH4 / diethyl ether / 1.5 h / Heating 3.1: NaH / tetrahydrofuran / 0.5 h / 20 °C 3.2: 69 percent / tetrahydrofuran / 28 h / Heating View Scheme

sodium periodate; RuO4 in tetrachloromethane; water; acetonitrile Ambient temperature;