Methyl iodide → 6-Methoxy-2-methyl-1-tetralone

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-methoxy-1-tetralone (5.0 g, 28.4 mmol), methyl iodide (20 mL, 262 mmol) and sodium hydride (60%, 5.5 g, 138 mmol, prewashed twice with hexanes) in toluene is heated at 80° C. for 3 days. The mixture is quenched carefully with water and is partitioned between EtOAc and brine. The organic extract is dried with MgSO4, concentrated and purified via column chromatography to give the title compound as a light yellow oil: 1H NMR (CDCl3) δ 1.27 (d, J=7 Hz, 3H), 1.83-1.89 (m, 1H), 2.10-2.15 (m, 1H), 2.51-2.60 (m, 1H), 2.90-3.00 (m, 2H), 3.85 (s, 3H), 6.68 (s, 1H), 6.81 (d, J=8.6 Hz, 1H), 8.01 (d, J=8.6 Hz, 1H).

Provenance & Evidence