Dimethyl Sulfate → Methyl 1-methoxy-2-naphthoate

Participants

Reaction Steps

To a solution of 1-hydroxy-naphthalene-2-carboxylic acid (5 g, 26.6 mmol) in acetone (100 mL) was added potassium carbonate (11 g, 79.72 mmol) followed by dimethyl sulfate (7.38 g, 58.46 mmol). The reaction mixture was refluxed overnight and then diluted with ethyl acetate (200 mL) and washed with water. The organic layer was dried (MgSO4), and the solvent was removed to give an oil (5.2 g): 1H NMR (CDCl3) δ 3.98 (s, 3H, CH3), 4.06 (s, 3H, CH3), 7.59 (m, 3H, Ar—H), 7.85 (m, 2H, Ar—H), 8.25 (m, 1H, Ar—H); MS 217 (M+1).

Provenance & Evidence