Hydrochloric Acid → Cyclopropane-1,2,3-tricarboxylic acid

HRID 54709Notes

Reaction equation

HRID 54709 reaction equation
[CH:1]1([C:12]([O:14]C)=[O:13])[CH:3]([C:4]([O:6]C)=[O:5])[CH:2]1[C:8]([O:10]C)=[O:9].[OH-].[Na+].Cl>CO>[CH:2]1([C:8]([OH:10])=[O:9])[CH:3]([C:4]([OH:6])=[O:5])[CH:1]1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12659895Trimethyl cyclopropane-1,2,3-tricarboxylate

Product 1

HCID 699248Cyclopropane-1,2,3-tricarboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethyl cyclopropane-1,2,3-tricarboxylate (20.6 g, 95.2 mmols) was dissolved in methanol (200 ml), followed by dropwise adding sodium hydroxide (23.7 g, 593 mmol) (dissolved in water (100 ml)) at room temperature, thereafter heating and reacting the mixture under reflux for one hour, cooling the reaction product, adding conc. hydrochloric acid (40 g, 1.1 mol), concentrating the reaction solution, adding acetone (200 ml) to the concentrated residue, heating the mixture under reflux for 2 hours, filtering off the precipitate, and concentrating the filtrate under reduced pressure, to obtain cyclopropane-1,2,3-tricarboxylic acid (16.0 g, 91.9 mmol, 97%).

Workup

  1. temperatureheating
  2. temperatureunder reflux for one hour
  3. temperaturecooling the reaction product
  4. concentrationconcentrating the reaction solution
  5. additionadding acetone (200 ml) to the concentrated residue
  6. temperatureheating the mixture
  7. temperatureunder reflux for 2 hours
  8. filtrationfiltering off the precipitate
  9. concentrationconcentrating the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c5fe50e6123044209265219794a0709b
Source dataset
uspto-grants-1997_04
Patent number
US05623078

Reaction notes

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