(2-Methyl-2-propenyl)succinic Anhydride → 3-isobutyldihydrofuran-2,5-dione

HRID 964967

Reaction equation

HRID 964967 reaction equation
[CH2:1]([CH:5]1[C:10](=[O:11])[O:9][C:7](=[O:8])[CH2:6]1)[C:2](=[CH2:4])[CH3:3].[H][H]>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([CH:5]1[CH2:6][C:7](=[O:8])[O:9][C:10]1=[O:11])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 225375(2-Methyl-2-propenyl)succinic AnhydrideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 104871113-isobutyldihydrofuran-2,5-dioneYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

β-Methallylsuccinic anhydride (539 g, 3.50 mole) was dissolved in toluene (800 mL) in a 1700 mL Parr stainless steel bottle fitted with a heating jacket. 10% Pd/C (3.60 g) was added and the bottle was connected to a Parr 2 L shaker fitted with two 4 L hydrogen tanks. After several evacuations and refilling with hydrogen, the shaker was started with the heater controlled for 60° C. The initial pressure was 60 lbs. When the pressure fell to 10 lbs, the tanks were repressurized to 60 lbs. After two hours, the controller was reset to 70° C. and the reaction was continued for another 12 hours. The heat was then turned off and after another 5 hours, the shaker was stopped. The reaction vessel was evacuated and the reaction mixture was filtered and concentrated. Distillation of the residue through the Vigreux column described above (P=9-10 mm Hg, T=180° C.) gave isobutylsuccinic anhydride (532.9 g, 97.6% yield).

Workup

  1. customfitted with a heating jacket
  2. customcontrolled for 60° C
  3. customwas reset to 70° C.
  4. waitthe reaction was continued for another 12 hours
  5. waitThe heat was then turned off and after another 5 hours
  6. customThe reaction vessel was evacuated
  7. filtrationthe reaction mixture was filtered
  8. concentrationconcentrated
  9. distillationDistillation of the residue through the Vigreux column
  10. customdescribed above (P=9-10 mm Hg, T=180° C.)

Sources & evidence

ORD record
ord-0a04128fbbdf4b71bc6b7a9887646f9b
Source dataset
uspto-grants-1998_06
Patent number
US05773438

Linked notes

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