Ethanol → 3-Phenyl-2,1-benzisoxazole-5-acetic acid

HRID 1199017Notes

Reaction equation

HRID 1199017 reaction equation
[C:1]1([C:7]2[O:8][N:9]=[C:10]3[CH:15]=[CH:14][C:13]([CH2:16][C:17]#N)=[CH:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[OH-:22].[Na+].[OH2:24]>>[C:1]1([C:7]2[O:8][N:9]=[C:10]3[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:24])=[O:22])=[CH:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 148353463-Phenyl-2,1-benzisoxazole-5-acetonitrile

Product 1

HCID 148353913-Phenyl-2,1-benzisoxazole-5-acetic acidYield 54%

Procedure

A solution of 5.0 g (0.021 mole) of 3-phenyl-2,1-benzisoxazole-5-acetonitrile, 100 ml of ethanol, and 10 ml of 20% sodium hydroxide was heated at reflux under a nitrogen atmosphere for 20 hr. The solution was poured into 800 ml of water, let stand for 0.5 hr and filtered. The filtrate was treated with charcoal, filtered, and the filtrate made acidic with concentrated hydrochloric acid. The mixture was allowed to stand at ambient temperature overnight and then filtered. The filter cake was washed with water, air dried, and recrystallized from 2-propanol to yield 2.9 g (54%) of gray powder, m.p. 173°-174° C. with decomposition.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 20 hr
  2. filtrationfiltered
  3. additionThe filtrate was treated with charcoal
  4. filtrationfiltered
  5. waitto stand at ambient temperature overnight
  6. filtrationfiltered
  7. washThe filter cake was washed with water, air
  8. customdried
  9. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-2198a4a148294a98bbb9e6b95d125ac7
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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