hydrogen in ethylene glycol dimethyl ether T=160°C; P=22502.3 Torr; 20 h; Inert atmosphereAutoclaveMolecular sieve;

sodium amide; benzene 16 h; Heating;

1: 89 percent / NaNH2/benzene / 16 h / Heating 2: 79 percent / 70percent sodium bis-(2-methoxyethoxy)aluminum hydride in toluene / benzene / 12 h / Ambient temperature View Scheme

in acetonitrile T=20°C; Substitution; rearrangement; elimination; 4 h;