4-Chlorobenzaldehyde → 2-(4-Chlorophenyl)-6-hydroxychroman-4-one

Participants

Reaction Steps

6-Hydroxy-2-(4-chlorophenyl)chroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 3.0 g of 2′,5′-dihydroxyacetophenone and 2.8 g of 4-chlorobenzaldehyde. The product was triturated from ethanol. 1H NMR (400 MHz, d6-DMSO) δ: 9.46 (s, 1H), 7.56 (d, 2H, J 8.5 Hz), 7.45 (d, 2H, J 8.5 Hz), 7.11 (d, 1H, J 2.8 Hz), 7.04 (dd, 1H, J 8.9, 2.8 Hz), 6.96 (d, 1H, J 8.9 Hz), 5.58 (dd, 1H, J 13.1, 2.9 Hz), 3.15 (dd, 1H, J −16.8, 13.1 Hz), 2.79 (dd, 1H, J −16.8, 2.9 Hz).

Provenance & Evidence