Methanol → (4-Aminophenyl)methanesulfonic acid

Participants

Reaction Steps

A 250 ml of Par hydrogenation bottle was charged 4-Nitrobenzyl Sulfonic Acid (6.80 g, 31.34 mmol), 10% Pd/C (0.4 g), CH3OH (150 ml) with few drop of water, and purged with hydrogen. The reaction mixture was shaken with 20 psi H2 over night. The catalyst was removed by filtration through celite and the solvent was evaporated. The crude compound was co-evaporated three times with 3×50 ml of water and crystallized with water/THF/EtAc/Toluene (1:10:10:100) to give 5.3 g (91%) of the title compound. 1H NMR (D2O), 7.28 (dd, 2H, J=2.2, 4.3 Hz), 6.95 (dd, 2H, J=2.2, 4.3 Hz), 4.10 (s, 2H); 13C NMR 134.30, 127.10, 121.04, 120.42, 59.14; MS m/z−186.35 (M−H).

Provenance & Evidence