Acetic Acid → 2-[5-(4-Chlorophenyl)-1,2-oxazol-3-yl]benzoic acid

HRID 1390797Notes

Reaction equation

HRID 1390797 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=3[C:15]([O:17]C)=[O:16])[CH:9]=2)=[CH:4][CH:3]=1.Cl.C(O)(=O)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=3[C:15]([OH:17])=[O:16])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 12789648HCID 12789648, compound

Product 1

HCID 123921152-[5-(4-Chlorophenyl)-1,2-oxazol-3-yl]benzoic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.8 g of methyl 2-[5-(4-chlorophenyl)3-isoxazolyl]benzoate, 12 ml of concentrated HCl, and 14 ml of acetic acid was held at reflux for 4 hours, cooled, diluted with water, and filtered to give 2.55 g (95%) of white solid, mp 174-176° C. Recrystallization of the solid gave 2.18 g of solid, mp 175.5-177.5° C.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-76e74cc7dfa846dba12be70f289f2032
Source dataset
uspto-grants-1979_02
Patent number
US04140515

Reaction notes

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