Acetone → 3-Buten-2-one,4-(3-fluorophenyl)-

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-fluorobenzaldehyde (4.0 ml, 37.7 mmol) and acetone (8.86 ml, 121 mmol) in water (10 ml), was added 0.25 M sodium hydroxide (15.08 ml, 3.77 mmol). The reaction mixture was heated at 65° C. for 2 h. The mixture was poured into ice water and extracted with ethyl acetate (200 ml). The organic layer was dried, filtered, and evaporated to give (E)-4-(3-fluorophenyl)but-3-en-2-one as yellow oil. It was used for the next reaction without purification (6.92 g, 42.1 mmol, 112% yield). 1H NMR (CDCl3/400 MHz): δ (ppm) 7.46 (d, 1H), 7.40-7.34 (m, 1H), 7.33-7.29 (m, 1H), 7.26-7.21 (m, 1H), 7.12-7.06 (m, 1H), 6.70 (d, 1H), 2.38 (s, 3H).

Provenance & Evidence