Ethanol → HCID 14835393, compound

HRID 1199019Notes

Reaction equation

HRID 1199019 reaction equation
[C:1]1([C:7]2[O:8][N:9]=[C:10]3[CH:15]=[C:14]([CH2:16][C:17]#N)[CH:13]=[CH:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:19].[Na+].C(O)C.[OH2:24]>>[C:1]1([C:7]2[O:8][N:9]=[C:10]3[CH:15]=[C:14]([CH2:16][C:17]([OH:24])=[O:19])[CH:13]=[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 14835352HCID 14835352, compound

Product 1

HCID 14835393HCID 14835393, compoundYield 66%

Procedure

A mixture of 2.9 g (0.012 mole) of crude 3-phenyl-2,1-benzisoxazole-6-acetonitrile, 10 ml of 20% sodium hydroxide, and 75 ml of ethanol was heated at reflux under a nitrogen atmosphere overnight. The dark solution was cooled and poured into 600 ml of water. The mixture was filtered through Celite, treated with charcoal and again filtered. The filtrate was made acidic with concentrated hydrochloric acid and a solid precipitated. The solid was collected by filtration, washed with water, dried, and recrystallized from 2-propanol (charcoal) to give 2.1 g (66%) of brown powder, m.p. 162°-177° C., with decomposition.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere overnight
  3. temperatureThe dark solution was cooled
  4. filtrationThe mixture was filtered through Celite
  5. additiontreated with charcoal
  6. filtrationagain filtered
  7. customa solid precipitated
  8. filtrationThe solid was collected by filtration
  9. washwashed with water
  10. customdried
  11. customrecrystallized from 2-propanol (charcoal)

Sources & evidence

ORD record
ord-6da8807f65954d688dfdbe6f1e3afdf1
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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