1: With methanol; lithium hydroxide; water in tetrahydrofuran T=20°C; 2 h; 2: With hydrogenchloride

1: 85 percent / NaH 2: 1.) sodium derivative / 2.) DME 3: 70 percent / 6N hydrochloric acid / acetic acid / 8 h 4: 1.) NaBH4, NaOH, 2.) hydrogen / 2.) 10percent Pd on carbon / 1. water, 2.) acetic acid View Scheme

1: 70 percent / 6N hydrochloric acid / acetic acid / 8 h 2: 1.) NaBH4, NaOH, 2.) hydrogen / 2.) 10percent Pd on carbon / 1. water, 2.) acetic acid View Scheme

hydrogenchloride; mercury; zinc in acetic acid; toluene Heating;

sodium hydroxide; sodium tetrahydroborate; hydrogen; palladium on activated charcoal 1. water, 2.) acetic acid; Yield given. Multistep reaction;