Maleic Anhydride → 4,7-Dimethyl-3a,4,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-1,3-dione

HRID 1879522Notes

Reaction equation

HRID 1879522 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH3:8][C:9]1[O:10][C:11]([CH3:14])=[CH:12][CH:13]=1>C(OCC)C>[CH3:8][C:9]12[O:10][C:11]([CH3:14])([CH:12]=[CH:13]1)[CH:3]1[CH:2]2[C:1](=[O:7])[O:6][C:4]1=[O:5]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 122662,5-Dimethylfuran

Product 1

HCID 2450364,7-Dimethyl-3a,4,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-1,3-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 100 mL 3-necked RBF is fitted with a mechanical stirrer, a condenser and a subaseal, and placed under nitrogen. Maleic anhydride (25.5 g, 0.260 mol) and anhydrous diethyl ether (35 mL) are charged to the RBF. 2,5-Dimethylfuran (27.7 mL, 0.260 mol) is added via syringe over a period of 20 mins to the suspension at 22° C. The reaction mixture is stirred for 18 h. The product is filtered off, washed with cold diethyl ether (100 mL), and dried under vacuum to yield the product 1 as a cream solid (36.32 g, 72%): 1H-NMR (300 MHz, CDCl3) δ6.35 (s, 2H), 3.16 (s, 2H), 1.76 (s, 6H).

Workup

  1. customA 100 mL 3-necked RBF is fitted with a mechanical stirrer, a condenser
  2. filtrationThe product is filtered off
  3. washwashed with cold diethyl ether (100 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-80cfb07883404c4eba5f89dec5cd008b
Source dataset
uspto-grants-2012_11
Patent number
US08318048B2

Reaction notes

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