1: With sodium tetrahydroborate in tetrahydrofuran 0.166667 h; 2: With iodine in tetrahydrofuran T=-10 - 20°C; Cooling with acetone-dry ice; 3: With ammonium chloride in tetrahydrofuran; chloroform; water

1: 93 percent / potassium hydride, 18-crown-6 / benzene / 2 h / Ambient temperature 2: 87 percent / LiAlH4 / diethyl ether / R.T, 2 h then reflux, 2 h View Scheme