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

HRID 325439

Reaction equation

HRID 325439 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1>O1C=CC=C1>[CH:4]12[O:6][CH:1]([CH:3]3[C:4](=[O:5])[O:6][C:1](=[O:7])[CH:2]31)[CH:2]=[CH:3]2

Participants

3

Reactant 1

HCID 7923Maleic Anhydride

Product 1

HCID 984843a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dioneYield 170%

Reagents, catalysts & solvents 1

HCID 8029FuranSolvent

Procedure

Maleic anhydride (50 g) and furan (150 ml) were heated under reflux for 1 hour, and then the excess of furan was distilled off. The residue was recrystallised from chloroform, yielding 72 g of 7-oxabicyclo [2.2.1]hept-2-ene-5,6-dicarboxylic acid anhydride (m.pt. 110° C., decomp.). This anhydride (40 g) and 30.75 g of 2-hydroxyethyl acrylate were heated in 250 ml of toluene at 100° C. for 3 hours, and then the toluene was distilled off under reduced pressure, leaving the desired compound as a viscous liquid.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationthe excess of furan was distilled off
  3. customThe residue was recrystallised from chloroform

Sources & evidence

ORD record
ord-ee81ebf605ea41feba46e0e8b08cc2a7
Source dataset
uspto-grants-1984_04
Patent number
US04440850

Linked notes

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