Isoprene → 3a,4,7,7a-Tetrahydro-5-methyl-1,3-isobenzofurandione

HRID 519249Notes

Reaction equation

HRID 519249 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]=[CH:9][C:10](=[CH2:12])[CH3:11]>O1CCCC1>[CH3:11][C:10]1[CH2:12][CH:2]2[CH:3]([CH2:8][CH:9]=1)[C:4](=[O:5])[O:6][C:1]2=[O:7]

Participants

4

Reactant 2

HCID 6557IsopreneHCID 7923Maleic Anhydride

Product 1

HCID 984963a,4,7,7a-Tetrahydro-5-methyl-1,3-isobenzofurandione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 5-L round bottom reaction flask fitted with a condenser was charged with maleic anhydride (C2H2(CO)2O) (500 g) and tetrahydrofuran (THF) (3 L) and isoprene (CH2═C(CH3)CH═CH2) (400 g) was then added at room temperature. The reaction was mildly exothermic. The reaction mixture was stirred at room temperature for about 2 hours till the Gas Chromatography (“GC”) analysis showed the consumption of maleic anhydride. The resulting mixture containing crude 5-methyl-3a,4,7,7a-tetrahydro-isobenzofuran-1,3-dione was used directly in the next step.

Workup

  1. customA 5-L round bottom reaction flask fitted with a condenser
  2. additionwas then added at room temperature
  3. customthe consumption of maleic anhydride
  4. additionThe resulting mixture containing crude 5-methyl-3a,4,7,7a-tetrahydro-isobenzofuran-1,3-dione

Sources & evidence

ORD record
ord-999d677e6fa64a9eb1ee44d5664f42be
Source dataset
uspto-grants-2015_08
Patent number
US09115330B2

Reaction notes

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