Acetic Acid → HCID 3529815, compound

Participants

Reaction Steps

Potassium hydroxide (2.0 9) was added to a suspension of estrone (1.352 g, 5.0 mmol) and 4-nitro-benzaldehyde (755 mg, 5.0 mmol) in ethanol (80 mL). The resulting dark brown solution was stirred for 4 hours at room temperature, then acetic acid (5 mL) and water (5 ml) were added (colour changes to orange). The product precipitated and was filtered off, washed with water (50 mL), ethanol (50 mL) and diethyl ether (50 mL) and dried under high vacuum. Yield: 1.682 g (83%) yellow solid. 1H-NMR (DMSO-d6, 400 MHz), δ: 0.93 (s, 3H, —CH3), 1.30-1.68 (m, 5H), 1.86-1.92 (m, 1H), 1.96-2.04 (m, 1H), 2.16-2.24 (m, 1H), 2.32-2.39 (m, 1H), 2.62-2.82 (m, 2H), 2.88-2.96 (m 1H), 6.46 (d, J=2.3 Hz, 1H), 6.52 (dd, J=8.6, 2.3 Hz, 1H), 7.06 (d, J=8.6 Hz, 1H), 7.42 (s, 1H), 7.92 (d, J=8.6 Hz, 2H), 8.27 (d, J=8.6 Hz, 2H), 9.04 (s, 1H, —OH). LRMS (FAB+): 404.1 (100, [M+H]+).

Provenance & Evidence