Potassium Carbonate → Nabumetone

Participants

Reaction Steps

4-(6-Methoxy-2-naphthyl)-but-3-en-2-one (100.0 g, 0.442 mol), (6.0 g), and potassium carbonate (13 g) were slurried in ethyl acetate (1100 mL), stirred 15 minutes, and 5% Pd/C (9.0 g) was added. The flask was purged with H2, a H2 balloon was added, and the reaction was followed by GC. After 12.5 hours, the reaction mass was filtered, washed with H2O (2×150 mL), dried (Na2SO4), filtered, and concentrated in vacuo, affording 95.3 g (95%) of nabumetone (93% purity, 98.5:1.5 ketone:alcohol ratio). The product was recrystallized from EtOH (275 mL) to give 81 g (80%) of 99% nabumetone (92% recovery of contained product). mp 79.5° C.; DSC 81.8° C.; 1H NMR (300 MHz, CDCl3) δ 7.61 (d,2H), 7.48 (s,1H), 7.22 (dd,1H), 7.12-7.04 (m,2H); 13C NMR (75 MHz, CDCl3) δ 208.2, 157.8, 136.6, 133.6, 129.6, 129.4, 128.0, 127.4, 126.7, 119.3, 106.2, 55.7, 45.5, 30.5, 30.2.

Provenance & Evidence