Hydrochloric Acid → HCID 20297516, compound

HRID 1389017Notes

Reaction equation

HRID 1389017 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][O:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)=[O:4].Cl>C(O)(=O)C>[F:19][C:16]([F:17])([F:18])[C:12]1[CH:11]=[C:10]([C:9]2[O:8][N:7]=[CH:6][C:5]=2[C:3]([OH:4])=[O:2])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20297499HCID 20297499, compound

Product 1

HCID 20297516HCID 20297516, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

A portion of the methyl-5-(3'-trifluoromethylphenyl)-4-isoxazolecarboxylate (5.0 g.; 0.018 mol.) in 10 ml. of acetic acid was reacted with 10 ml. of concentrated hydrochloric acid at reflux for six hours. The reaction mixture was cooled to 25° C., and then poured onto 50 g. of ice. The resulting mixture was extracted five times with 25 ml. of methylene chloride. The extracts were combined, dried over magnesium sulfate, filtered, and concentrated to yield a white solid. Recrystallization from ether-hexane yielded 5-(3'-trifluoromethylphenyl)-4-isoxazolecarboxylic acid.

Workup

  1. additionpoured onto 50 g
  2. extractionThe resulting mixture was extracted five times with 25 ml
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a white solid
  7. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-810203b2e4944b58926502c882cb8744
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

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