2-Methoxy-1,4-Naphthoquinone → 2-Methoxy-1,4-diacetyloxynaphthalene

Participants

Reaction Steps

A solution of 2-methoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the calculated amount of hydrogen was absorbed, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the catalyst was filtered off and solvent evaporated from the filtrate. The residue was dissolved in ether (100 mL), washed with 1M hydrochloric acid (3×50 mL) and then with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2-methoxy-1,4-diacetyloxynaphthalene, m.p. 135°-136° C.

Provenance & Evidence