sodium methylate in methanol 1) 1.5h, 0 deg C 2) room temperature 3) 24h, reflux;

1: 74 percent / LiAlH4 / diethyl ether; benzene / 3 h / Heating 2: 94 percent / PBr3, LiBr / diethyl ether / 17 h / Ambient temperature 3: 87 percent / 24 h / Ambient temperature 4: 34 percent / NaOMe / methanol / 1) 1.5h, 0 deg C 2) room temperature 3) 24h, reflux View Scheme

1: 87 percent / 24 h / Ambient temperature 2: 34 percent / NaOMe / methanol / 1) 1.5h, 0 deg C 2) room temperature 3) 24h, reflux View Scheme

1: 94 percent / PBr3, LiBr / diethyl ether / 17 h / Ambient temperature 2: 87 percent / 24 h / Ambient temperature 3: 34 percent / NaOMe / methanol / 1) 1.5h, 0 deg C 2) room temperature 3) 24h, reflux View Scheme