Methyl 3-hydroxynaphthalene-1-carboxylate → Methyl 3-hydroxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

Participants

Reaction Steps

A mixture of methyl 3-hydroxy-1-naphthalenecarboxylate (5.77 g, 28.5 mmol) and 10% Pd/C (1.57 g) in HOAc (140 mL) was hydrogenated on a Parr apparatus at 60° C., and 50 psi for 21 h. After filtration through a pad of diatomaceous earth the solvent was removed in vacuo and the residue treated with water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water, dried (MgSO4) and concentrated to yield product as a yellow oil (5.24 g, 89%). 1H NMR (CDCl3) δ 7.20 (d, 1H), 6.73 (d, 1H), 3.86 (s, 3H), 2.94 (d, 2H), 2.76 (d, 2H), 1.74 (m, 4H); MS m/z 205 (M−H).

Provenance & Evidence