Acetic Acid → HCID 13302824, compound

HRID 1670357Notes

Reaction equation

HRID 1670357 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:8]([F:24])([F:23])[C:9]([F:22])([F:21])[O:10][C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[S:13]([F:16])(=[O:15])=[O:14].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(O)(=O)C>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]1([C:8]([C:9]([O:10][C:11]([C:12]([S:13]([F:16])(=[O:14])=[O:15])([F:17])[F:18])([F:19])[F:20])([F:22])[F:21])([F:24])[F:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 241BenzeneHCID 7187Benzoyl PeroxideHCID 27751695-Iodoperfluoro-3-oxapentanesulfonyl fluoride

Product 1

HCID 13302824HCID 13302824, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

7.82 g (100 mmol) of benzene, 8.52 g (20 mmol) of 5-iodooctafluoro-3-oxapentanesulfonyl fluoride, 4.84 g (20 mmol) of benzoyl peroxide, 0.36 g (2 mmol) of copper (II) acetate, and 100 mL of acetic acid were refluxed for 4 hrs at 115° C. Then the mixture was stirred at room temperature overnight. The mixture was diluted with water (˜100 mL), and the product was extracted with hexane and washed with water until neutral pH was obtained. The solvent was removed to yield dark yellow oil. The product was purified by distillation under reduced pressure (˜27 inch Hg). The first faction was composed of a mixture of the product plus iodobenzene (2.8 g, approximately 1:1 ratio). The second fraction consisted of 2.1 g of pure product (colorless oil) (28% yield).

Workup

  1. extractionthe product was extracted with hexane
  2. washwashed with water until neutral pH
  3. customwas obtained
  4. customThe solvent was removed
  5. customto yield dark yellow oil
  6. distillationThe product was purified by distillation under reduced pressure (˜27 inch Hg)
  7. additionThe first faction was composed of a mixture of the product plus iodobenzene (2.8 g, approximately 1:1 ratio)

Sources & evidence

ORD record
ord-066adc7b877546e78bd1dbc9b0ef0664
Source dataset
uspto-grants-2011_08
Patent number
US07993797B2

Reaction notes

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