Trifluoroacetic anhydride → HCID 14143437, compound

HRID 53127Notes

Reaction equation

HRID 53127 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:3][CH:2]=1.F[C:15](F)(F)[C:16](OC(=O)C(F)(F)F)=[O:17]>C1C=CC=CC=1>[C:16]([O:12][C:10]1[C:3]2[C:4](=[CH:5][CH:6]=[C:1]([CH3:13])[CH:2]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:17])[CH3:15]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 782794-p-Tolylbutyric acid

Product 1

HCID 14143437HCID 14143437, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a 2 liter round-bottomed flask equipped with condenser and a nitrogen inlet were added 98.3 grams (0.552 mol) 4-(p-tolyl)butyric acid and 900 mL dry benzene. After the acid had dissolved, 132.6 mL (0.939 mol) trifluoroacetic anhydride was added dropwise over 35 minutes. The reaction was then refluxed for 20 hours (starting material confirmed to be consumed by thin layer chromatography (tlc), Rf 0.1 to 0.6 (DNP +ve) in 2/1 ethyl acetate (EtOAc)/hexane) cooled, and evaporated to remove most of the trifluoroacetic acid. The reside was taken up in ethyl acetate, washed with dilute aqueous ammonium hydroxide, water and brine, dried over sodium sulfate, and evaporated. The resulting solid was suitable for use in the next step.

Workup

  1. customTo a 2 liter round-bottomed flask equipped with condenser and a nitrogen inlet
  2. dissolutionAfter the acid had dissolved
  3. temperatureThe reaction was then refluxed for 20 hours
  4. custom(starting material confirmed to be consumed by thin layer chromatography (tlc), Rf 0.1 to 0.6 (DNP +ve) in 2/1 ethyl acetate (EtOAc)/hexane)
  5. temperaturecooled
  6. customevaporated
  7. customto remove most of the trifluoroacetic acid
  8. washwashed with dilute aqueous ammonium hydroxide, water and brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-8242ada32b7945eebce433b9c5ce2558
Source dataset
uspto-grants-1997_04
Patent number
US05618811

Reaction notes

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