Acetic Acid → Perfluorophenyl acetate

HRID 446179Notes

Reaction equation

HRID 446179 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[F:5][C:6]1[C:11](O)=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=1[F:16].C1(N=C=NC2CCCCC2)CCCCC1>CCOC(C)=O>[F:5][C:6]1[C:11]([O:3][C:1](=[O:4])[CH3:2])=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=1[F:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 13041Pentafluorophenol

Product 1

HCID 87968Perfluorophenyl acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 0.40 M solution of acetic acid (46 μL, 0.800 mmol) in EtOAc (2.00 mL, filtered through activated alumina) were added pentafluorophenol (162 mg, 0.880 mmol) and 1,3-dicyclohexylcarbodiimide (182 mg, 0.88 mmol). The reaction mixture was stirred for 12 h at rt at which time it was filtered (washing with EtOAc) and concentrated. Ester 19 was used immediately without further purification.

Workup

  1. filtrationwas filtered
  2. wash(washing with EtOAc)
  3. concentrationconcentrated
  4. customEster 19 was used immediately without further purification

Sources & evidence

ORD record
ord-bbaa0589e0ef4f21b38aa3eec71002f4
Source dataset
uspto-grants-2013_07
Patent number
US08476451B2

Reaction notes

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