Hydrochloric Acid → Trans 2-carboethoxy-3-carboxy-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

To a stirred solution of trans 2,3-dicarboethoxy-1,2,3,4-tetrahydronaphthalene (2.1 g, 7.6 mmol) in ethanol (10 mL) at room temperature under nitrogen was added 1.0 M aqueous sodium hydroxide solution (7.6 mL, 7.6 mmol). After 16 h, 1.0 M aqueous hydrochloric acid solution (10 mL) was added to quench the reaction mixture. Upon completion of addition, the reaction mixture was concentrated under vacuum to yield a residue. The residue was diluted with ethyl acetate. The organic layer was washed with 1.0 M aqueous hydrochloric acid solution, saturated aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and concentrated under vacuum to yield a residue. The residue was purified by silica gel chromatography (50% ethyl acetate in hexane was used) to yield the title compound (1.37 g, 73%). 13C NMR (400 MHz, (CD3)2CO) δ 175.7, 174.7, 135.0, 134.9, 129.3, 129.2, 127.0, 61.0, 42.8, 42.5, 32.2, 14.4. 1H NMR (400 MHz, (CD3)2CO) δ 7.02 (s, 4H), 4.03 (m, 2H), 2.74-3.09 (m, 6H), 1.13 (t, J=7.0 Hz, 6H). MS [M+Na]+, 271.

Provenance & Evidence