Sodium Hydroxide → 2-p-Chlorophenyl-5-(2,5-dimethylphenoxy)-4-oxazoleacetic acid

HRID 46768Notes

Reaction equation

HRID 46768 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([O:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=3[CH3:26])=[C:11]([CH2:13][C:14]([O:16]C)=[O:15])[N:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([O:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=3[CH3:26])=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20385655HCID 20385655, compound

Product 1

HCID 203856742-p-Chlorophenyl-5-(2,5-dimethylphenoxy)-4-oxazoleacetic acidYield 72.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 13 g of methyl 2-p-chlorophenyl-5-(2,5-dimethylphenoxy)-4-oxazoleacetate prepared in Example 4 in 150 ml of acetone at room temperature was dropwise added a 15 ml aqueous solution of 2.0 g of sodium hydroxide. The mixture was further stirred for 3.5 hours. After the solvent was evaporated under reduced pressure, water was added to the remaining aqueous solution. The resulting solution was cooled and acidified to pH 3 with hydrochloric acid. The crystalline precipitate was filtered off and recrystallized from ethanol to give 9.05 g of the title compound as bulky needles, melting at 185° C.

Workup

  1. customAfter the solvent was evaporated under reduced pressure, water
  2. additionwas added to the remaining aqueous solution
  3. temperatureThe resulting solution was cooled
  4. filtrationThe crystalline precipitate was filtered off
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2f261490df9f4084ba563ae7f2b4df4d
Source dataset
uspto-grants-1979_11
Patent number
US04175130

Reaction notes

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