Hydrochloric Acid → (E)-3-(3,4-Dimethoxyphenyl)-1-(3-hydroxyphenyl)-1-propenone

Participants

Reaction Steps

A solution of 3,4-dimethoxybenzaldehyde AP17380 (400 g, 2.41 moles) and 3′-hydroxyacetophenone AP17381 (328 g, 2.41 moles) in EtOH (3200 mL) was treated with a solution of aqueous KOH (536 g, 1200 mL) over a 1 hour period. The resulting solution was allowed to stir for 16 h at room temperature. The reaction mixture was then treated with EtOH (2000 mL) followed by water (1200 mL). A solution of EtOH/water (3400 mL, 1:1) was then added and the reaction mixture acidified to pH 6 using concentrated HCl (720 mL). After addition of acid, water (4000 mL) was added to induce precipitation. The resulting mixture was left stirring overnight and the solids then filtered, washed with water (2×900 mL) and then hexane (2×800 mL). The product was dried under vacuum for 3 hours and then placed in a vacuum oven at 50° C. for 6 days to provide AP14894 (609 g, 89%) as a yellow solid: mp 138-139° C.; TLC (EtOAc/hexane, 1:1) Rf=0.35; 1H NMR (DMSO-d6, 300 MHz) 9.85 (br s, 1H), 7.71 (d, J=6.6 Hz, 2H), 7.61 (d, J=7.7 Hz, 1H), 7.53 (d, J=1.7 Hz, 1H), 7.47 (d, J=1.7 Hz, 1H), 7.39-7.34 (m, 2H), 7.07-7.00 (m, 2H), 3.87 (s, 3H), 3.82 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) 189.4, 158.2, 151.6, 149.4, 144.7, 139.7, 130.1, 127.9, 124.2, 120.4, 120.2, 119.7, 115.0, 112.0, 111.2, 56.1, 56.0; LRMS (ES+) (M+H)+285; Anal. Calcd for C17H16O4: C, 71.82; H, 5.67. Found: C, 71.55; H, 5.61.

Provenance & Evidence