Synthesis
General procedure for the synthesis of 3-(bromomethyl)-4-methylfuran-2,5-dione from 3-(bromomethyl)-4-methylfuran-2,5-dione: To 2-bromomethyl-3-methylmaleic anhydride (1.25 g, 6.10 mmol) was added 5 M aqueous sodium hydroxide (4 mL) at room temperature and the mixture was stirred for 12 hours. The reaction mixture was adjusted to pH 1 with 5 M hydrochloric acid (5 mL), sodium chloride was added and extracted three times with ethyl acetate. The combined organic layers were concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate, 2:1) to afford 227 mg of 3-(hydroxymethyl)-4-methylfuran-2,5-dione as an oil (yield: 26%).1H NMR (CDCl3) δ 2.21 (t, J = 1.1Hz, 3H), 4.63 (q, J = 1.1Hz, 2H).
References
[1] Synthesis, 1999, # 8, p. 1306 - 1308
[2] Patent: US2008/90825, 2008, A1. Location in patent: Page/Page column 27
[3] Patent: US2008/275057, 2008, A1. Location in patent: Page/Page column 76
