1: 88.8 percent / 1) NaBH4; 2) 10 percent aq. NaOH / 0.5 h / Ambient temperature 2: 79.7 percent / 1) Jones reagent; 2) 10 percent aq. NaOH, aq. HCl / acetone / 0.5 h / 0 °C View Scheme

xylene

1: 88.8 percent / 1) NaBH4; 2) 10 percent aq. NaOH / 0.5 h / Ambient temperature 2: 79.7 percent / 1) Jones reagent; 2) 10 percent aq. NaOH, aq. HCl / acetone / 0.5 h / 0 °C 3: 0.371 g / H2O / 1 h / 50 - 60 °C 4: 61.9 percent / sodium hydride / hexamethylphosphoric acid triamide / 3.5 h / Ambient temperature View Scheme

sodium hydroxide; sodium tetrahydroborate 0.5 h; Ambient temperature;

sodium hydroxide; sodium tetrahydroborate in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=50 - 60°C; 2 h;