p-Toluenesulfonic acid → Fluazifop-methyl

HRID 1589716Notes

Reaction equation

HRID 1589716 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:21]=[CH:20][C:13]([O:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[C:24]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[F:23][C:2]([F:22])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:21]=[CH:20][C:13]([O:14][CH:15]([CH3:19])[C:16]([O:18][CH3:24])=[O:17])=[CH:12][CH:11]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 91701Fluazifop

Product 1

HCID 155294Fluazifop-methyl

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture containing 12.46 g of 2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid and a catalytic amount of p-toluenesulfonic acid in 70 ml of methanol is boiled under reflux for 4 hours. After evaporating the solution to dryness, the residue is dissolved in ether and washed with sodium hydrogen carbonate solution. The ethereal layer is separated, dried over anhydrous magnesium sulfate and evaporated to dryness to give 11.5 g of product.

Workup

  1. temperatureunder reflux for 4 hours
  2. customAfter evaporating the solution to dryness
  3. dissolutionthe residue is dissolved in ether
  4. washwashed with sodium hydrogen carbonate solution
  5. customThe ethereal layer is separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-f8e726d69cf241e8bb121d3d6f0052ab
Source dataset
uspto-grants-1993_04
Patent number
US05199970

Reaction notes

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