Cyclohexanediacetic acid → 1,1-Cyclohexanediacetic Anhydride

HRID 2223833Notes

Reaction equation

HRID 2223833 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=[O:13])([CH2:7][C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(OC(=O)C)(=O)C>[C:1]12([CH2:7][C:8](=[O:10])[O:14][C:12](=[O:13])[CH2:11]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2

Participants

3

Reactant 1

HCID 78061Cyclohexanediacetic acid

Product 1

HCID 27342891,1-Cyclohexanediacetic AnhydrideYield 110.4%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 1,1-cyclohexane diacetic acid (20.0 g) in acetic anhydride (20 mL) was heated under reflux for 5 hours. The solution was concentrated under reduced pressure, and the residue was concentrated three times azeotropically with benzene. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=2:1) to give the title compound (20.1 g).

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationThe solution was concentrated under reduced pressure
  3. concentrationthe residue was concentrated three times azeotropically with benzene
  4. customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-f3bbe5119d5d4dd689ea83b550ece734
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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