Sodium Hydroxide → 5-Benzyl-3-dodecylisoxazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-phenyl-2,4-hexanedione (66.5 g, 0.201 mol), hydroxylamine hydrochloride (27.9 g, 0.402 mol), and 1M sodium hydroxide (201 mL, 0.201 mol) in glacial acetic acid (1.5 L) was stirred at 65° C. under nitrogen for 23 hours. The solution was allowed to cool, and the resulting suspension was filtered off and washed with CH3CO2H-H2O (9:1). The filtercake was washed separately with H2O and dried under house vacuum/air stream to give a white crystalline solid containing the title compound and 5-dodecyl-3-(phenylmethyl)isoxazole; yield 41.8 g (64%); mp 41°-43° C. Additional product was obtained by reheating the CH3CO2H filtrate and washings to 60° C.; adding H2O (150 mL) dropwise until cloudy, and following the previous procedure; yield 15.2 g (23%).

Provenance & Evidence