Ethanol → 3-(4-Chlorophenyl)-2,1-benzisoxazole-7-acetic acid

HRID 1199021Notes

Reaction equation

HRID 1199021 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][N:10]=[C:11]3[C:16]([CH2:17][C:18]#N)=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][CH:3]=1.[OH-:20].[Na+].C(O)C.[OH2:25]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][N:10]=[C:11]3[C:16]([CH2:17][C:18]([OH:25])=[O:20])=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 156347583-(4-Chlorophenyl)-2,1-benzisoxazole-7-acetonitrile

Product 1

HCID 156347603-(4-Chlorophenyl)-2,1-benzisoxazole-7-acetic acidYield 38%

Procedure

A mixture of 3.9 g (0.015 mole) of 3-(4-chlorophenyl)-2,1-benzisoxazol-7-acetonitrile, 10 ml of 20% sodium hydroxide and 75 ml of 95% ethanol was heated at reflux under a nitrogen atmosphere for 17 hr. The mixture was poured into 600 ml of water and filtered. The filtrate was treated with charcoal and filtered through Celite. The filtrate was adjusted to pH 7 with concentrated hydrochloric acid and the mixture filtered. The filtrate was made acidic with concentrated hydrochloric acid and a solid precipitated. The solid was collected by filtration and recrystallized from 2-propanol to yield 1.6 g (38%) of pale-yellow needles, m.p. 200°-202° C. with decomposition.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 17 hr
  3. filtrationfiltered
  4. additionThe filtrate was treated with charcoal
  5. filtrationfiltered through Celite
  6. filtrationthe mixture filtered
  7. customa solid precipitated
  8. filtrationThe solid was collected by filtration
  9. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-dee418807be844e18e44f3c1e906ceba
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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