Hydrochloric Acid → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-9-carboxylic acid

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Reaction Steps

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester (1.03 g, 2.71 mmol), Methanol (20.0 mL), tetrahydrofuran (2 mL), and lithium hydroxide aqueous (5 mL), stir at reflux. After 18 hours, add 5N HCl until reaction is acidic, then extract with ethyl acetate and wash with brine. Dry the organic phase with anhydrous sodium sulfate then concentrate to yield the titled compound (0.97 g, 97%) as a white solid. TLC Rf=0.41 in 3% methanol in DCM. 1H NMR (DMSO): 12.30 (s, 1H), 7.25 (m, 3H), 6.92 (m, 3H), 6.82 (dd, 1H, J=8.6, 2.4 Hz), 4.18 (d, 1H, J=12.3 Hz), 3.76 (m, 6H), 3.42 (dd, 1H, J=12.6, 2.4 Hz), 3.27 (s, 1H), 2.50 (m, 1H), 1.89 (m, 1H), 1.59 (m, 2H), 1.40 (m, 1H), 1.23 (m, 1H), 0.99 (m, 3H); MS m/z 322 (M−44, decarbonylation).

Provenance & Evidence