Acetic Acid → HCID 86751590, compound

HRID 2293731Notes

Reaction equation

HRID 2293731 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[N:15][N:14]([C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])[C:13]=3[CH:22]=2)[CH:5]=[C:4]([F:23])[C:3]=1[C:24]([F:27])([F:26])[F:25].[O-][Mn](=O)(=O)=O.[K+].[N+](=C)=[N-].[C:37](O)(=[O:39])C>O.CO.O1CCCC1.C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[N:15][N:14]([C:17]([CH3:21])([CH3:20])[C:18]([O:39][CH3:37])=[O:19])[C:13]=3[CH:22]=2)[CH:5]=[C:4]([F:23])[C:3]=1[C:24]([F:27])([F:26])[F:25]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 516875Potassium PermanganateHCID 86751591HCID 86751591, compound

Product 1

HCID 86751590HCID 86751590, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy]-β,β-dimethyl-1H-benzotriazole-1-ethanol (2.2 g, 0.00545 mole) in acetic acid and water is stirred at 56°-80° C., treated portionwise with solid KMnO4 (8.5 g, 0.054 mole) over a 3 hour period, cooled and filtered. The filtrate is concentrated in vacuo to give a gum residue. The residue is chromatographed on silica gel with 15% tetrahydrofuran in chloroform to afford a white solid, 1.2 g. The solid is dissolved in methanol, treated with a solution of diazomethane in tetrahydrofuran, heated on a steam bath and concentrated in vacuo to give a solid residue. Chromatography of the residue using silica gel and 5% tetrahydrofuran in carbon tetrachloride as eluant affords the title product as a white solid, 0.65 g, mp 76.8°-80° C., identified by elemental and NMR analyses.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated in vacuo
  4. customto give a gum residue
  5. customThe residue is chromatographed on silica gel with 15% tetrahydrofuran in chloroform
  6. customto afford a white solid, 1.2 g
  7. temperatureheated on a steam bath
  8. concentrationconcentrated in vacuo
  9. customto give a solid residue

Sources & evidence

ORD record
ord-2732893cdabc489b9ee01720dc52ebea
Source dataset
uspto-grants-1997_11
Patent number
US05686617

Reaction notes

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