Ethyl Acetate → 1-Methoxy-2-naphthalenemethanol

Participants

Reaction Conditions

Reaction Steps

The product of Step A (4.5 g, 20.83 mmol) was dissolved in anhydrous tetrahydrofuran (100 mL) and cooled to 0° C. To this solution was added a 1 M solution of lithium aluminum hydride in tetrahydrofuran (31 mL). The mixture was stirred at this temperature for 30 min, allowed to warm up to room temperature, and stirred for an additional 30 min. Ethyl acetate (200 mL) was then added carefully to the reaction mixture to destroy the excess of lithium aluminum hydride. The mixture was then diluted with a 1 M solution of aqueous hydrogen chloride (100 mL), the organic layer was separated, dried (MgSO4), and concentrated to give an oil (4.1 g) which solidified: 1H NMR (CDCl3) δ 3.97 (s, 3H, CH3), 4.89 (s, 2H, CH2), 7.51 (m, 3H, Ar—H), 7.60 (m, 1H, Ar—H), 7.82 (m, 1H, Ar—H), 8.07 (m, 1H, Ar—H); MS (GC/MS) 188.

Provenance & Evidence