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

Participants

Reaction Steps

2-(2-Chlorophenyl)-6-hydroxychroman-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 2-chlorobenzaldehyde. The product was passed though silica gel using heptane-ethyl acetate as an eluant and then triturated with ethanol. 1H NMR (400 MHz, d6-DMSO) δ: 9.49 (s, 1H), 7.77 (dd, 1H, J 7.7, 2.0 Hz), 7.53 (dd, 1H, J 7.6, 1.8 Hz), 7.49-7.41 (m, 2H), 7.14 (d, 1H, J 2.9 Hz), 7.06 (dd, 1H, J 8.8, 2.9 Hz), 6.93 (d, 1H, J 8.8 Hz), 5.78 (dd, 1H, J 13.6, 2.6 Hz), 3.19 (dd, 1H, J −16.9, 13.6 Hz), 2.78 (dd, 1H, J −16.9, 2.6 Hz).

Provenance & Evidence