7-Methoxy-3,4-dihydronaphthalene-1-carbonitrile → 7-Methoxynaphthalene-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-methoxy-3, 4-dihydronaphthalene-1-carbonitrile (9.95 g, 53.1 mmol) in p-cymene (1600 mLs) was added 10% Pd/C (5 g), the reaction mixture was stirred and heated to 150° C. overnight. The mixture was cooled and the catalyst removed by filtering through filter aid. The p-cymene was removed on the rotovap with the vacuum pump, giving a liquid which solidified on standing. The solid was slurried in hexane, filtered and dried to afford a-white solid (4.3 g, 44%). A portion was purified further by silica gel (10% ethyl acetate-hexanes) to produce a white solid: mp 77–78° C.; 1H NMR (DMSO-d6): δ 3.97 (3H, s), 7.36 (1H, s), 7.39 (1H, d, J=2.5 Hz), 7.52 (1H, t, J=7.4 Hz), 8.04–8.13 (2H, m), 8.24 (1H, d, J=8.2 Hz).

Provenance & Evidence