Acetic Anhydride → 1,1-Cyclohexanediacetic Anhydride

HRID 342743Notes

Reaction equation

HRID 342743 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>>[CH2:4]1[CH2:3][CH2:2][C:1]2([CH2:7][C:8](=[O:10])[O:14][C:12](=[O:13])[CH2:11]2)[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 78061Cyclohexanediacetic acid

Product 1

HCID 27342891,1-Cyclohexanediacetic Anhydride

Procedure

To a 100-mL round-bottomed flask was added 1,1-cyclohexanediacetic acid (2.03 g, 9.99 mmol) and acetic anhydride (11.6 mL). The reaction mixture was held at reflux for 2 hours, and then cooled to room temperature. Volatiles were removed via vacuum distillation (0.1 Torr, 20°-60° C.). The resulting crude product was dried under vacuum (0.1 Torr) at 80° C. for 14 hours to yield the title compound as a white solid which was used without further purification (1.75 g, 96%).

Workup

  1. temperatureat reflux for 2 hours
  2. customVolatiles were removed via vacuum distillation (0.1 Torr, 20°-60° C.)
  3. dry with materialThe resulting crude product was dried under vacuum (0.1 Torr) at 80° C. for 14 hours

Sources & evidence

ORD record
ord-e5fe71e025b64909bd0eacd70766ca18
Source dataset
uspto-grants-1999_01
Patent number
US05859047

Reaction notes

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