Methanol → HCID 66652017, compound

Participants

Reaction Steps

Combine 6-hydroxy-10-(4-hydroxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-9-carboxylic acid (0.903 g, 2.67 mmol), AcCl (2 mL), and methanol (20.0 mL), and reflux under nitrogen atmosphere. After 72 hours, concentrate reaction to dryness under vacuum, add ethyl acetate and water. Separate the organic phase and wash with brine. Dry the organic phase with anhydrous sodium sulfate and concentrate to yield the titled compound (0.980 g, 99%) as a brown solid. 1H NMR (d-methanol): 7.15 (d, 2H, J=8.4 Hz), 7.04 (d, 1H, J=8.8 Hz), 6.91 (s, 1H), 6.77 (d, 2H, J=8.4 Hz), 6.64 (m, 1H), 4.32 (d, 1H, J=12.8 Hz), 3.58 (s, 3H), 3.45 (dd, 1H, J=12.6, 2.4 Hz), 3.34 (s, 1H), 2.52 (d, 1H, J=14.1 Hz), 1.97 (m, 1H), 1.68 (m, 2H), 1.44 (m, 2H), 1.11 (m, 3H); MS m/z 351 (M−1).

Provenance & Evidence