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

HRID 2090079Notes

Reaction equation

[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[O:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1>C1(C)C=CC=CC=1>[CH:9]12[O:8][CH:12]([CH:11]=[CH:10]1)[CH:3]1[CH:2]2[C:1](=[O:7])[O:6][C:4]1=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

temperatureThe mixture was then cooled to room temperature
filtrationAfter 1 h the resulting white crystals were filtered off
washthe solid washed with 2×30 mL of petroleum ether

Sources & evidence

ORD record: ord-f525b8ee7bcf4289b778248acadf76ef
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436104B2

Reaction notes

Loading…