Acetic Anhydride → Acetyl trifluoroacetate

HRID 1068066Notes

Reaction equation

HRID 1068066 reaction equation
CC(OC(C)=O)=O.[C:8]([O:14][C:15]([C:17](F)(F)F)=[O:16])([C:10]([F:13])([F:12])[F:11])=[O:9]>>[F:11][C:10]([F:13])([F:12])[C:8]([O:14][C:15](=[O:16])[CH3:17])=[O:9]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 9845Trifluoroacetic anhydride

Product 1

HCID 12752924Acetyl trifluoroacetate

Procedure

Acetyl trifluoroacetate was prepared by the method of Bourne in which equimolar amounts of Ac2O and TFAA are combined and heated to reflux for an hour, then fractionally distilled and the material boiling between 90-100° C. collected and characterized by IR and NMR: 1H NMR (CDCl3): δ 2.39 ppm; 13C NMR (CDCl3): δ 162.7,158.7 (q, JCF=44.7 Hz), 113.9 (q, JCF=286.3 Hz), 22.0 ppm; IR (CH2Cl2) VC═O=1854,1782; vC—O—C=1075 cm−1.

Workup

  1. temperatureheated
  2. temperatureto reflux for an hour
  3. distillationfractionally distilled
  4. customboiling between 90-100° C.
  5. customcollected

Sources & evidence

ORD record
ord-9efaf63ed3a34b49b50cc17eea3d0ce4
Source dataset
uspto-grants-2001_06
Patent number
US06248923B1

Reaction notes

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