Ethyl acetate hexane → 2-Isopropyl-3-methylmaleic anhydride

HRID 1774385Notes

Reaction equation

HRID 1774385 reaction equation
O[C:2]([CH:11]([CH3:13])[CH3:12])([CH:6]([CH3:10])[C:7]([OH:9])=[O:8])[C:3](O)=[O:4].CCCCCC.C(OCC)(=O)C>C(OC(=O)C)(=O)C>[CH:11]([C:2]1[C:3]([O:8][C:7](=[O:9])[C:6]=1[CH3:10])=[O:4])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 861023272-Hydroxy-2-isopropyl-3-methylsuccinic acid

Product 1

HCID 537842412-Isopropyl-3-methylmaleic anhydrideYield 40%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
110 °C

Procedure

The 2-hydroxy-2-isopropyl-3-methylsuccinic acid thus obtained was dissolved in acetic anhydride (30 mL), and stirred at 110° C. for 15 h. The acetic anhydride was evaporated under reduced pressure, and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 19:1) to give 203 mg of the title compound as oil (yield: 40%).

Workup

  1. customThe acetic anhydride was evaporated under reduced pressure
  2. customthe residue thus obtained

Sources & evidence

ORD record
ord-9179c2db645f4b619453b65d7c7b0a01
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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