Acetic Acid → 2,4-Dioxo-3-oxabicyclo[3.1.0]hexane-6-carboxylic acid

HRID 54710Notes

Reaction equation

HRID 54710 reaction equation
C(O)(=O)C.C(OC(=O)C)(=O)C.[CH:12]1([C:21]([OH:23])=[O:22])[CH:14]([C:15]([OH:17])=[O:16])[CH:13]1[C:18]([OH:20])=O>>[O:22]=[C:21]1[O:23][C:18](=[O:20])[CH:13]2[CH:12]1[CH:14]2[C:15]([OH:17])=[O:16]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 699248Cyclopropane-1,2,3-tricarboxylic acid

Product 1

HCID 199597242,4-Dioxo-3-oxabicyclo[3.1.0]hexane-6-carboxylic acidYield 83%

Procedure

Acetic acid (58.8 ml, 933 mmol) and acetic anhydride (20.4 ml, 185 mmol) were added to cyclopropane-1,2,3-tricarboxylic acid (24.4 g, 140 mmol), followed by reacting the mixture while heating under reflux for 2 hours, concentrating the reaction solution into a half volume, filtering off deposited crystals, washing them with heptane and drying under reduced pressure, to obtain 2,4-dioxo-3-oxabicyclo[3.1.0]hexane-6-carboxylic acid (18.1 g, 116 mmol, 83%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrating the reaction solution into a half volume
  4. filtrationfiltering off
  5. washwashing them with heptane
  6. customdrying under reduced pressure

Sources & evidence

ORD record
ord-208c34ede0fa48c4bf3257c4af8ec1be
Source dataset
uspto-grants-1997_04
Patent number
US05623078

Reaction notes

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