Acetic Anhydride → 1,1-Cyclohexanediacetic Anhydride

HRID 1611920Notes

Reaction equation

HRID 1611920 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 2

HCID 7918Acetic AnhydrideHCID 78061Cyclohexanediacetic acid

Product 1

HCID 27342891,1-Cyclohexanediacetic AnhydrideYield 99%

Procedure

1,1-Cyclohexanediacetic acid (4 g, 20 mmol) and acetic anhydride (3.8 mL, 40 mmol) were heated under reflux until a clear solution was obtained (˜1 h), and heating continued for a further hour to ensure the reaction had gone to completion. The mixture was cooled to room temperature and the solvent removed in vacuo to afford 1,1-cyclohexanediacetic anhydride (37) (3.6 g, 99% yield). Electrospray mass spectrometry showed the expected molecular ion at m/z=183.2 (M+H+).

Workup

  1. temperatureunder reflux until a clear solution
  2. customwas obtained (˜1 h)
  3. temperatureheating
  4. waitcontinued for a further hour
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-76c3205b72c94b2fb6a7f5e9220c4e3c
Source dataset
uspto-grants-2006_01
Patent number
US06992076B2

Reaction notes

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