Sodium Hydroxide → HCID 13015763, compound

HRID 652844Notes

Reaction equation

HRID 652844 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]2[C:11]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)=[N:12][O:13][C:9]=2[C:8]=1[Cl:21])C.[OH-].[Na+].[Na]>C(O)C>[Cl:21][C:8]1[C:9]2[O:13][N:12]=[C:11]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[C:10]=2[CH:19]=[CH:20][C:7]=1[O:6][CH2:5][C:4]([OH:22])=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5360545SodiumHCID 14012478HCID 14012478, compound

Product 1

HCID 13015763HCID 13015763, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a boiling suspension of 15.0 g of ethyl[(7-chloro-3-(2-furyl)-1,2-benzisoxazol-6-yl)oxy]acetate, Example 7, in 500 ml of boiling 95% ethyl alcohol there is added 10 ml of a 50% sodium hydroxide solution causing the sodium salt to precipitate out almost immediately. An additional 300 ml of 95% ethyl alcohol is added and boiling is maintained for 30 minutes. The reaction mixture is permitted to cool slightly, after which 100 ml of a 5% hydrochloric acid solution is added thereto. The product begins to separate with cooling, 250 ml of water is added and the diluted mixture is chilled with ice. The precipitate is collected by filtration and recrystallized from isopropyl alcohol to yield the product {[7-chloro-3-(2-furyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid having a melting point of 230° to 233° C.

Workup

  1. customto precipitate out almost immediately
  2. additionAn additional 300 ml of 95% ethyl alcohol is added
  3. temperatureboiling is maintained for 30 minutes
  4. temperatureto cool slightly
  5. additionafter which 100 ml of a 5% hydrochloric acid solution is added
  6. customto separate
  7. temperaturewith cooling
  8. addition250 ml of water is added
  9. temperaturethe diluted mixture is chilled with ice
  10. filtrationThe precipitate is collected by filtration
  11. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-157db5ea90bb462e9ce64d6acc5cb0d2
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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