Reaction #82988

Reaction equation

Acetic acid

acetic anhydride

cyclopropane-1,2,3-tricarboxylic acid

→

2,4-dioxo-3-oxabicyclo[3.1.0]hexane-6-carboxylic acid

Yield 83.0%

Conditions

Workup

1. 1
   Temperaturewhile heating
2. 2
   Temperatureunder reflux for 2 hours
3. 3
   Concentrationconcentrating the reaction solution into a half volume
4. 4
   Filtrationfiltering off
5. 5
   Washwashing them with heptane
6. 6
   Otherdrying under reduced pressure

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%).

Source