Hydrochloric Acid → HCID 13015715, compound

HRID 1156797Notes

Reaction equation

HRID 1156797 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][N:14]=2)=[C:9]([Cl:22])[C:8]=1[Cl:23])C.Cl>C(O)C.[OH-].[Na+]>[O:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:24])=[O:3])=[C:8]([Cl:23])[C:9]=2[Cl:22])=[N:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13015714HCID 13015714, compound

Product 1

HCID 13015715HCID 13015715, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 6.88 g (0.187 m) of ethyl-4-(1,2-benzisoxazol-3-yl)-2,3-dichlorophenoxyacetate of Example 2D in 70 ml of ethanol, 4 ml of 10 N NaOH is added. The mixture is refluxed for 1 hour. The salt which forms is filtered off, and combined with 250 ml of water at 90° C., giving a suspension. Concentrated HCl is added until the mixture is acidic. The mixture is stirred 1 hour at ambient temperature and the product is filtered off. The crude product is recrystallized from ethanol/H2O and then recrystallized from toluene to give 4.1 g (65%) of pure 4-(1,2-benzisoxazol-3-yl)-2,3-dichlorophenoxyacetic acid, m.p. 166°-167° C.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. filtrationThe salt which forms is filtered off
  3. customcombined with 250 ml of water at 90° C.
  4. customgiving a suspension
  5. filtrationthe product is filtered off
  6. customThe crude product is recrystallized from ethanol/H2O
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-b3e5c62a62804b57b4ea8c551f999aed
Source dataset
uspto-grants-1982_06
Patent number
US04337261

Reaction notes

Loading…