1-Naphthalenesulfonic acid 3-benzyloxy-5-methylphenyl ester → 5-Methyl-3-(1-naphthalenylsulfonyloxy)phenol

Participants

Reaction Steps

A mixture of 1-naphthalenesulfonic acid 3-benzyloxy-5-methylphenyl ester (1.0 g, 2.47 mmol), as prepared in the preceding step, and 10% palladium on carbon (200 mg) in ethanol (20 mL) was hydrogenated (balloon) overnight. The catalyst was removed by filtration through diatomaceous earth (methanol washes) and the filtrate was evaporated in vacuo to give the title compound as a colorless syrup (705 mg, 91%). 1H-NMR (300 MHz, CDCl3) δ 2.11 (s, 3H), 4.20 (bs, 1H), 6.16 (t, 1H), 6.47 (t, 1H), 7.51 (t, 1H), 7.69 (t, 1H), 7.79 (t, 1H), 7.81 (d, 1H), 8.11 (dt, 2H), 8.77 (dd, 1H).

Provenance & Evidence