Acetyl chloride → 1,1-Cyclohexanediacetic Anhydride

HRID 1193544Notes

Reaction equation

HRID 1193544 reaction equation
C(Cl)(=O)C.[C:5]1([CH2:15][C:16]([OH:18])=[O:17])([CH2:11][C:12]([OH:14])=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>>[C:5]12([CH2:11][C:12](=[O:14])[O:18][C:16](=[O:17])[CH2:15]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 78061Cyclohexanediacetic acid

Product 1

HCID 27342891,1-Cyclohexanediacetic Anhydride

Conditions

Temperature
100 °C

Procedure

Acetyl chloride (35 ml 492 mmol) was added to 1,1 cyclohexanediacetic acid (25 g, 125 mmol) in a round bottom flask and the suspension was heated for 3 hrs. at 60° C. using an oil bath. After about 15 min. the suspension became clear. The reaction was attached to a short path condenser and was heated to 100° C. under vacuum to remove volatile by-products. 1HNMR indicated no starting diacid and GC indicated >99% purity. Upon cooling to room temperature the anhydride solidified. 1H-NMR (CDCl3): δ2.65(s,4H); 1.45(m,lOH)

Workup

  1. temperaturethe suspension was heated for 3 hrs
  2. customat 60° C.
  3. customThe reaction was attached to a short path condenser
  4. customto remove volatile by-products
  5. temperatureUpon cooling to room temperature the anhydride

Sources & evidence

ORD record
ord-a7f7fec3e57241e7a1eb25584cb0d016
Source dataset
uspto-grants-1989_03
Patent number
US04810778

Reaction notes

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