Sulfuric Acid → HCID 18694881, compound

HRID 1871056Notes

Reaction equation

HRID 1871056 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[O:16][N:15]=[CH:14][C:13]=2[CH3:17])=[C:10]([Cl:18])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].S(=O)(=O)(O)O>O1CCOCC1>[Cl:1][C:2]1[C:11]([C:12]2[O:16][N:15]=[CH:14][C:13]=2[CH3:17])=[C:10]([Cl:18])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 18694867HCID 18694867, compound

Product 1

HCID 18694881HCID 18694881, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 20 ml dioxane, was dissolved methyl 2,4-dichloro-3-(4-methylisoxazol-5-yl)benzoate in an amount of 0.83 g, and the resulting solution was then added with concentrated sulfuric acid in an amount of 5 ml and subsequently stirred for 15.5 hours under reflux and heating. After cooling the mixture, dioxane therein was distillated out, and the mixture was then extracted with ethyl acetate. The organic layer obtained was washed with saturated saline solution, then dried with anhydrous magnesium sulfate. The solvent in the layer was condensed under reduced pressure, and the residue obtained was purified by using a silica gel column chromatography to obtain an objective product, 2,4-dichloro-3-(4-methylisoxazol-5-yl)benzoic acid in an amount of 0.48 g in crystalline form. The melting point of the product was found to be in a range of 248-252° C.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. extractionthe mixture was then extracted with ethyl acetate
  4. customThe organic layer obtained
  5. washwas washed with saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customcondensed under reduced pressure
  8. customthe residue obtained
  9. customwas purified

Sources & evidence

ORD record
ord-690312c0084646fe9b54faef74a816ad
Source dataset
uspto-grants-2000_08
Patent number
US06100421

Reaction notes

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