Acetic Anhydride → Acetonedicarboxylic acid anhydride

HRID 276123

Reaction equation

HRID 276123 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=[O:3])C.[CH2:8](C(O)=O)[C:9](CC(O)=O)=[O:10]>C(O)(=O)C>[CH3:8][C:9]([CH:6]1[C:1](=[O:3])[O:4][C:5]1=[O:7])=[O:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68328Acetonedicarboxylic acid

Product 1

HCID 54573794Acetonedicarboxylic acid anhydrideYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 60 ml of acetic acid and 43 ml of acetic anhydride at 0° C., was added slowly 40 g (0.27 mol) of acetonedicarboxylic acid. The mixture was stirred and the temperature was not allowed to rise above 10° C. The acid was dissolved slowly and a pale yellow precipitate formed. After 3 h the product was filtered, washed with 30 ml of glacial acetic acid and 100 ml of benzene. The white powder obtained was dried at high vacuum to afford 30 g of acetonedicarboxylic acid anhydride (yield 86%). Mp 137-138° C.

Workup

  1. customto rise above 10° C
  2. dissolutionThe acid was dissolved slowly
  3. customa pale yellow precipitate formed
  4. filtrationAfter 3 h the product was filtered
  5. washwashed with 30 ml of glacial acetic acid and 100 ml of benzene
  6. customThe white powder obtained
  7. customwas dried at high vacuum

Sources & evidence

ORD record
ord-960ae6dbf3fa45d3b8b2109797f3961d
Source dataset
uspto-grants-2002_03
Patent number
US06353105B1

Linked notes

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