Maleic Anhydride → 3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

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Reaction Conditions

Reaction Steps

Maleic anhydride (30.00 g, 0.306 mol) was suspended in 150 mL of toluene and the mixture warmed to 80° C. Furan (33.4 mL, 0.459 mol) was added via syringe and the turbid solution stirred for 6 h. The mixture was then cooled to room temperature and the stirring was stopped. After 1 h the resulting white crystals were filtered off and the solid washed with 2×30 mL of petroleum ether. Obtained 44.40 g (0.267 mol, 87% yield) of the desired product as small white needless. m.p. 124-127° C. (dec.) IR (neat): 1857, 1780, 1309, 1282, 1211, 1145, 1083, 1019, 947, 920, 902, 877, 847, 800, 732, 690, 674, 633, 575 cm−1. 1H NMR (400.03 MHz, CDCl3, 298 K) δ=3.17 (s, 2H, CH), 5.45 (t, J=1.0 Hz, 2H, CHO); 6.57 (t, J=1.0 Hz, 2H, CHvinyl). 13C{1H}NMR (100.59 MHz, CDCl3, 298 K) δ=48.85 (2C, CH), 82.35 (2H, CHO), 137.12 (2C, CHvinyl) 170.04 (2C, CO). Anal. Calcd. for C8H6O4: C, 57.84; H, 3.64. Found C, 57.74; H, 3.68.

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