1,3-Cyclohexanedicarboxylic acid → 3-Oxabicyclo[3.3.1]nonane-2,4-dione

HRID 1960004

Reaction equation

HRID 1960004 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

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

  1. temperaturerefluxed during 5 h
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was then dissolved in a mixture of heptane (20 ml) and toluene (20 ml)
  4. temperaturethe solution was cooled to 4° C
  5. filtrationThe precipitated solid was then collected by filtration
  6. washwashed with pentane

Sources & evidence

ORD record
ord-bce6e23ff0424e538dad968377196ac2
Source dataset
uspto-grants-2013_04
Patent number
US08410282B2

Linked notes

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