Methane → HCID 14835392, compound

Participants

Reaction Steps

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.

Provenance & Evidence