Dimethyl Carbonate → 3,4-Dihydro-2-hydroxynaphthalenecarboxylic Acid, Methyl Ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-tetralone (25.0 g, 171 mmol) in dry tetrahydrofuran (250 ml) at 0° C. under argon was added lithium diisopropylamide (111 ml, 2M solution, 222 mmol). After stirring at 0° C. for 1 h, dimethyl carbonate was added (145 ml, 1710 mmol). After stirring at 0° C. for 0.5 h, the reaction mixture was warmed to room temperature, and then heated at reflux for 16 h. The mixture was then cooled to 0° C. and quenched with hydrochloric acid (1M, 450 ml). The resulting mixture was extracted with ethyl acetate (3×1000 ml) and the combined extracts were washed with brine (1000 ml) then dried (Na2SO4) and evaporated in vacuo to afford the title compound as a dark brown oil (36.3 g, 100%).

Provenance & Evidence