Hexane → HCID 117899762, compound

HRID 522458Notes

Reaction equation

HRID 522458 reaction equation
[F:1][C:2]([F:26])([F:25])[S:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([CH3:23])=[CH:13][C:12]=1[CH3:24].ClC1C=CC=C(C(OO)=[O:35])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].CCCCCC>C(Cl)(Cl)Cl.C(OCC)(=O)C>[F:26][C:2]([F:1])([F:25])[S:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([S:17]([CH2:18][C:19]([F:20])([F:21])[F:22])=[O:35])[C:14]([CH3:23])=[CH:13][C:12]=1[CH3:24]

Participants

7

Reactant 4

HCID 8058HexaneHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 117899644HCID 117899644, compound

Product 1

HCID 117899762HCID 117899762, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 40 ml of chloroform was dissolved 1.36 g (3.23 mmol) of 6-trifluoromethylthiohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl]ether. Thereto was added 0.67 g (2.72 mmol) of 3-chloroperbenzoic acid (purity: about 70%) under ice cooling, and the mixture was stirred for 30 minutes at room temperature. Then, saturated aqueous solution of sodium thiosulfate was added to the reaction mixture to decompose excess peroxide. Thereafter, the solvent was distilled off under reduced pressure, and extraction was conducted by adding ethyl acetate and water. The organic phase obtained was washed by aqueous potassium carbonate solution and saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=5:1), to obtain 0.87 g (yield: 62%) of an intended product.

Workup

  1. distillationThereafter, the solvent was distilled off under reduced pressure, and extraction
  2. additionby adding ethyl acetate and water
  3. customThe organic phase obtained
  4. washwas washed by aqueous potassium carbonate solution and saturated aqueous sodium chloride solution in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-d54876e292cc4ed980a1a9d75f49e479
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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