Methyl 3-hydroxynaphthalene-1-carboxylate → Methyl 3-hydroxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2>CC(O)=O.[Pd]>[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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).