1: NaOH / methanol / 40 h / 25 °C 2: 72 percent / hydroxylamine hydrochloride / butan-1-ol / 6 h / Heating 3: 87 percent / KMnO4 / acetone / 96 h / 25 °C 4: 71 percent / diphenyl ether / 220 °C View Scheme

acetoxy(2,6-bis((diphenylphosphino)methyl)-3,5-dimethylphenyl)palladium(II); potassium carbonate; butan-1-ol 0.5 h; Reflux; chemoselective reaction;

Hydrogenation;

1: NaOH / methanol / 40 h / 25 °C 2: 72 percent / hydroxylamine hydrochloride / butan-1-ol / 6 h / Heating 3: 87 percent / KMnO4 / acetone / 96 h / 25 °C View Scheme