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

HRID 1482732

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

Participants

Conditions

Temperature: 80 °C

Procedure

Protected-maleimide functional initiator was synthesized by following literature.4 Maleic anhydride (10.0 g, 0.1 mol) was suspended in 30 mL of toluene and the mixture warmed to 80° C. Furan (11.3 mL, 0.15 mol) was added via syringe and the turbid solution was stirred for overnight. The mixture was then cooled to ambient temperature white solids formed during standing were collected by filtration and washed with 2×30 mL of diethyl ether afforded 3a,4,7,7a-tetrahydro-4,7-epoxyisobenzofuran-1,3-dione (1) as white needless. Yield: 12.35 g (74%). 1H NMR (500 MHz, CDCl3, δ) 6.55 (s, 2H, CH═CH, bridge protons), 5.45 (s, 2H, —CHO, bridge-head protons), 3.15 (s, 2H, CH—CH, bridge protons). 13C NMR (CDCl3, δ): 169.9, 137.0, 82.2, 48.7.

Workup

customProtected-maleimide functional initiator was synthesized
temperatureThe mixture was then cooled to ambient temperature white solids
customformed
filtrationduring standing were collected by filtration
washwashed with 2×30 mL of diethyl ether

Sources & evidence

ORD record: ord-26fb1d2cd6df42abba7ac44d9883ecfb
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09415123B2

Linked notes

Loading…