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

HRID 1482732

Reaktionsgleichung

Reaktionsgleichung von HRID 1482732
[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]

Komponenten

4

Edukt 2

HCID 7923Maleic AnhydrideHCID 8029Furan

Produkt 1

HCID 984843a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-26fb1d2cd6df42abba7ac44d9883ecfb
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09415123B2

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