Ethyl 4-iodobenzoate (200 g, 0.725 mol) and acryl alcohol (63 g, 1.087 mol) were added with stirring to a DMF (600) containing sodium bicarbonate (152 g, 1.812 mol), tetrabutylammonium bromide (117 g, 0.362 mol) and palladium(II) acetate (3.2 g, 0.014 mol) in a 600 mL) in suspension. The reaction mixture was heated to 75-80 °C and kept at this temperature for 3-3.5 h. The reaction was subsequently cooled to 40-50 °C. Under vigorous stirring, toluene (1 L) was added to the reaction mixture and stirring was continued for 15 minutes. The mixture was filtered through a diatomaceous earth pad and the diatomaceous earth pad was washed with toluene (2 x 200 mL). The filtrate and washings were combined, washed with water (3 x 1 L) and then evaporated to constant weight at 30-40 °C and 10 mmHg. 147.5 g (98.8% yield, 84% HPLC purity) of ethyl 4-(3-oxopropyl)benzoate crude product was obtained as a dark brown oil, which could be used in the next step without further purification.1H NMR (DMSO-d6): δ 1.38 (t, 3H), 2.81 (t, 2H), 3.03 (t, 2H), 4.39 (q, 2H) , 7.27 (d, 2H), 7.98 (d, 2H), 9.81 (s, 1H).
