Ethanol → HCID 14835395, compound

HRID 1199020Notes

Reaction equation

HRID 1199020 reaction equation
[CH3:1][CH:2]([C:5]1[C:13]2[C:9](=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11][N:12]=2)[CH:8]=[CH:7][CH:6]=1)[C:3]#N.[OH-:20].[Na+].C([OH:24])C>O>[CH3:1][CH:2]([C:5]1[C:13]2[C:9](=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11][N:12]=2)[CH:8]=[CH:7][CH:6]=1)[C:3]([OH:24])=[O:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14835359HCID 14835359, compound

Product 1

HCID 14835395HCID 14835395, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.7 g (0.031 mole) of α-methyl-3-phenyl-2,1-benzisoxazole-7-acetonitrile, 20 ml of 20% sodium hydroxide and 150 ml of 95% ethanol was heated at reflux and under an argon atmosphere for 21 hr. The reaction mixture was poured into 1.2 liters of water and filtered. The filtrate was treated with charcoal and filtered through Celite. The filtrate pH was adjusted to 7 with concentrated hydrochloric acid and filtered. The filtrate pH was adjusted to 2 with concentrated hydrochloric acid and allowed to stand at ambient temperature. The resulting solid was collected by filtration, air-dried, and recrystallized from cyclohexane-ethyl ether to give 2.6 g (31%) of light-tan solid, m.p. 140°-144° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux and under an argon atmosphere for 21 hr
  3. filtrationfiltered
  4. additionThe filtrate was treated with charcoal
  5. filtrationfiltered through Celite
  6. filtrationfiltered
  7. customto stand at ambient temperature
  8. filtrationThe resulting solid was collected by filtration
  9. customair-dried
  10. customrecrystallized from cyclohexane-ethyl ether

Sources & evidence

ORD record
ord-3aa9937421a64858b668db806d73da51
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

Loading…