1,3-Cyclohexanedicarboxylic acid → 3-Oxabicyclo[3.3.1]nonane-2,4-dione
Reaction equation
[CH:1]1([C:10]([OH:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=O)[CH2:2]1>C(OC(=O)C)(=O)C>[CH:1]12[CH2:2][CH:3]([CH2:4][CH2:5][CH2:6]1)[C:7](=[O:9])[O:12][C:10]2=[O:11]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
10 g (58.2 mmol) 1,3-cyclohexane dicarboxylic acid were suspended in acetic anhydride (40 ml) and refluxed during 5 h. The solution was then cooled to room temperature and the solvents were removed in vacuo. The residue was then dissolved in a mixture of heptane (20 ml) and toluene (20 ml) and the solution was cooled to 4° C. The precipitated solid was then collected by filtration and washed with pentane to give 5.9 g of the titled compound as white needles.
Workup
- temperaturerefluxed during 5 h
- customthe solvents were removed in vacuo
- dissolutionThe residue was then dissolved in a mixture of heptane (20 ml) and toluene (20 ml)
- temperaturethe solution was cooled to 4° C
- filtrationThe precipitated solid was then collected by filtration
- washwashed with pentane
Sources & evidence
- ORD record
- ord-bce6e23ff0424e538dad968377196ac2
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410282B2
Reaction notes
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