Methane → HCID 14835392, compound

HRID 1199018Notes

Reaction equation

HRID 1199018 reaction equation
CC([C:5]1[CH:6]=[CH:7][C:8]2[C:9]([CH:19]=1)=[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:11][N:12]=2)C#N.[OH-:20].[Na+].[CH2:22]([OH:24])[CH3:23].[CH4:25]>C(OCC)C>[CH3:25][CH:23]([C:5]1[CH:6]=[CH:7][C:8]2[C:9]([CH:19]=1)=[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:11][N:12]=2)[C:22]([OH:20])=[O:24]

Participants

6

Reactant 4

HCID 297MethaneHCID 702EthanolHCID 14798Sodium HydroxideHCID 14835350HCID 14835350, compound

Product 1

HCID 14835392HCID 14835392, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.5 g (0.0302 mole) of α-methyl-3-phenyl-2,1-benzisoxazole-5-acetonitrile, 25 ml of 10% sodium hydroxide solution and 160 ml of ethanol was stirred and heated at reflux under an argon atmosphere for 20 hr. The solvents were evaporated under reduced pressure and the residue was partitioned between water (250 ml) and ethyl ether (100 ml). The layers were separated and the aqueous layer was extracted twice with 200 ml portions of ethyl ether. The aqueous layer was treated with charcoal and filtered through Celite. The filtrate pH was adjusted to 2 with concentrated hydrochloric acid. The mixture was extracted with methylene chloride (900 ml) and the organic layer was washed twice with 300 ml portions of water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 4.2 g of a brownish, viscous residue that solidified upon standing. The solid was dissolved in 400 ml of ethyl ether, treated with charcoal and filtered. The filtrate was evaporated under reduced pressure to give a solid. The solid was recrystallized from isopropyl ether-petroleum ether (30°-60° C.) to give 3.6 g (44%) of bright-yellow solid, m.p. 145°-149° C.

Workup

  1. temperatureheated
  2. temperatureat reflux under an argon atmosphere for 20 hr
  3. customThe solvents were evaporated under reduced pressure
  4. customthe residue was partitioned between water (250 ml) and ethyl ether (100 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted twice with 200 ml portions of ethyl ether
  7. additionThe aqueous layer was treated with charcoal
  8. filtrationfiltered through Celite
  9. extractionThe mixture was extracted with methylene chloride (900 ml)
  10. washthe organic layer was washed twice with 300 ml portions of water
  11. dry with materialdried over magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customto give 4.2 g of a brownish, viscous residue that
  14. filtrationfiltered
  15. customThe filtrate was evaporated under reduced pressure
  16. customto give a solid
  17. customThe solid was recrystallized from isopropyl ether-petroleum ether (30°-60° C.)

Sources & evidence

ORD record
ord-4b8a2d532a6d4960982c378146b9a396
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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