Acetic Anhydride → 1,1-Cyclohexanediacetic Anhydride

HRID 227340Notes

Reaction equation

HRID 227340 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-2b67861576314e4ebf8b42096805df53
Source dataset
uspto-grants-2009_07
Patent number
US07560483B2

Reaction notes

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