lithium aluminium tetrahydride in tetrahydrofuran T=25°C; 1 h;

1: 1,4-dimethoxy-2-hydroxymethylnaphthalene With n-butyllithium in tetrahydrofuran; hexane T=-78 - 20°C; Metallation; 1 h; 2: methyl iodide in tetrahydrofuran; hexane Methylation; 0.333333 h; Further stages.;

in tetrahydrofuran; water

1.1: 92 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 20 °C 2.2: 57 percent / tetrahydrofuran; hexane / 0.33 h View Scheme