1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 2: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 3: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C 4: 96 percent / NaClO2; 2-methyl-2-butene; aq. NaH2PO4 / 2-methyl-propan-2-ol / 3 h / 20 °C View Scheme

1: 98 percent / H+ / methanol 2: 97 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether / 200 °C View Scheme

hydrogen cation in methanol Hydrolysis;

1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 2: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 3: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

1: Jone's reagent / acetone / 0 - 4 °C 2: sulfuric acid / 20 °C 3: hydrogen; ethylenediamine / ethanol; water View Scheme

Jone's reagent in acetone T=0 - 4°C;