Acetic Acid → HCID 20297501, compound

HRID 1389019Notes

Reaction equation

HRID 1389019 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[O:5])C.C(O)(=O)C.Cl>O>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:10]1[O:9][N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 22221209HCID 22221209, compound

Product 1

HCID 20297501HCID 20297501, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl-5-(2',4'-dichlorophenyl)-4-isoxazolecarboxylate (50.0 g.; 0.17 mol.) was dissolved in 250 ml. of glacial acetic acid. To the mixture was added 250 ml. of hydrochloric acid and the resultant solution was rapidly stirred at 100° C. for 4 hours. The mixture was then allowed to cool and poured into 2 liters of water. The resultant precipitate was collected, dried, and recrystallized from pentane to yield 5-(2',4'-dichlorophenyl)-4-isoxazolecarboxylic acid (40.0 g.; 93.6% yield) having a melting point of 122°-123° C. and the following analysis:

Workup

  1. additionTo the mixture was added 250 ml
  2. temperatureto cool
  3. customThe resultant precipitate was collected
  4. customdried
  5. customrecrystallized from pentane

Sources & evidence

ORD record
ord-67f38574cec34ef089b6a2b168f733ff
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

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