Methanol → 1-Carbomethoxy-6-chloro-3,4-dihydronaphthalene

Participants

Reaction Steps

6-Chloro-1-cyano-3,4-dihydronaphthalene (5 g, 263 mmol), lit ref, was dissolved in 77% sulfuric acid in methanol and the resulting solution was heated at 95°-100° C. for 2.5 h. The reaction mixture was allowed to cool to ambient temperature and 45 mL was added, followed by 5 mL of water. The reaction mixture was stirred at ambient temperature for 2 days and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was concentrated in vacuo. The residue was purified by chromatography on silica gel eluted with 20% ethyl acetate in hexane to give 1.53 g (26% yield) of the title compound; MS DCI-NH3M/Z: 240 (M+H)+ ; 1H NMR (CDCl3) δ2.37-2.45 (2H, m), 2.75 (2H, t, J=7.5 Hz), 3.85 (3H, s), 7.15 (1H, d, J=1.5 Hz), 7.15 (1H, d, 9 Hz), 7.2 (1H, d, J=7.5 Hz), 7.77 (1H, d, J=7.5).

Provenance & Evidence