Acetic Acid → 2-[3-(3-Trifluoromethylphenyl)-5-Isoxazolyl]Benzoic Acid

HRID 903791Notes

Reaction equation

HRID 903791 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]([O:18]C)=[O:17])[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.C(O)(=O)C.Cl>O>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]([OH:18])=[O:17])[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 13018699Methyl 2-[3-(3-trifluoromethylphenyl)-5-isoxazolyl]benzoate

Product 1

HCID 127896382-[3-(3-Trifluoromethylphenyl)-5-Isoxazolyl]Benzoic AcidYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.20 g of methyl 2-[3-(3-trifluoromethylphenyl)-5-isoxazolyl]benzoate, 75 ml. of acetic acid, and 50 ml. of concentrated HCl was held at reflux for 4 hours, cooled, and poured into 450 ml. of cold water. The resultant solid was recrystallized from CH3CN to give 3.87 g of solid, mp 176°-177° C.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturecooled
  3. additionpoured into 450 ml
  4. customThe resultant solid was recrystallized from CH3CN

Sources & evidence

ORD record
ord-baaa0a85bfbe4811a7661aa31c25f90b
Source dataset
uspto-grants-1980_10
Patent number
US04229204

Reaction notes

Loading…