Sodium Hydroxide → 2-{[3-(4-Chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}butyric acid

HRID 568710Notes

Reaction equation

HRID 568710 reaction equation
C([O:3][C:4](=[O:25])[CH:5]([O:8][C:9]1[CH:24]=[CH:23][C:12]2[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:14][O:15][C:11]=2[CH:10]=1)[CH2:6][CH3:7])C.[OH-].[Na+]>CO>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[C:12]3[CH:23]=[CH:24][C:9]([O:8][CH:5]([CH2:6][CH3:7])[C:4]([OH:25])=[O:3])=[CH:10][C:11]=3[O:15][N:14]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14012534Ethyl 2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}butyrate

Product 1

HCID 140125352-{[3-(4-Chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}butyric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.6 g of ethyl-2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}butyrate, 30 ml of 15% sodium hydroxide solution and 30 ml of methanol, is stirred under reflux for 3 hr. The methanol is evaporated and the solution is poured into dilute hydrochloric acid/ice affording a flocculate precipitate. The precipitate is collected, dried in vacuo and recrystallized from toluene to afford 2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}butyric acid, mp 144° C.

Workup

  1. temperatureunder reflux for 3 hr
  2. customThe methanol is evaporated
  3. additionthe solution is poured into dilute hydrochloric acid/ice affording a flocculate precipitate
  4. customThe precipitate is collected
  5. customdried in vacuo
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-4de55766d5b24938bcb00afc641824ed
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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