Benzene → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,10a-hexahydro-phenanthrene

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Reaction Steps

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ol (184.3 mg, 0.54 mmol), p-toluene sulfonic acid (20.0 mg, 0.11 mmol), benzene (5 mL), stir, and reflux under nitrogen atmosphere. After 1.5 hours, cool reaction to ambient temperature, add ethyl acetate, wash sat sodium bicarbonate solution (aq), and then with brine, dry over sodium sulfate, and concentrate in vacuum. Flash chromatograph using 0% to 20% ethyl acetate/hexanes to yield the titled compound (147.6 mg, 85%) as a clear oil. TLC Rf=0.51 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.53 (d, 2H, J=8.8 Hz), 7.10 (d, 1H, J=7.9 Hz), 6.93 (m, 3H), 6.72 (m, 2H), 3.85 (m, 6H), 3.21 (m, 1H), 2.79 (m, 1H), 2.49 (m, 1H), 1.80 (m, 1H), 1.58 (m, 4H), 1.30 (m, 2H).

Provenance & Evidence