4-(2-Hydroxy-1-decyloxy)nitrobenzene → 4-(2-Hydroxy-1-decyloxy)aniline

Participants

Reaction Steps

4-(2-hydroxy-1-decyloxy)nitrobenzene (20 g, 0.68 mol) was dissolved in ethyl acetate (200 mL) and 10 palladium on carbon (2.5 g) was added to a Parr pressure bottle. The contents were then hydrogenated at 50 psi until hydrogen uptake ceased. The catalyst was removed by suction filtration through a pad of Celite. Removal of solvent afforded 4-(2-hydroxy-1-decyloxy)aniline in quantitative yield (18.0 g, 0.68 mol, 100% yield) as a tan solid. The structure was confirmed by NMR and mass spectroscopy.

Provenance & Evidence