Acetic Anhydride → 1,1-Cyclohexanediacetic Anhydride

HRID 584538

Reaction equation

HRID 584538 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 100%

Procedure

A suspension of 1,1-cyclohexanediacetic acid (39.95 mmol) in acetic anhydride (159.8 mmol) was refluxed gently until a clear solution was obtained (ca. 1 h). The reaction mixture was kept at reflux for another hour until the reaction was complete. The reaction mixture was cooled to room temperature and acetic acid and excess acetic anhydride were removed under vacuum to afford 7.28 g (100%) of (3). 1H NMR (CDCl3): 2.65 (4H, s); 1.54-1.43 (10H, m).

Workup

  1. temperaturewas refluxed gently until a clear solution
  2. customwas obtained (ca. 1 h)
  3. temperatureat reflux for another hour until the reaction
  4. customacetic acid and excess acetic anhydride were removed under vacuum

Sources & evidence

ORD record
ord-edd7d89b78ef47a1bc1b7863bfd26112
Source dataset
uspto-grants-2005_08
Patent number
US06927036B2

Linked notes

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