Ethyl Acetoacetate → HCID 178429254, compound

Participants

Reaction Steps

A solution of ethyl acetoacetate (26 g) and cyclohexylhydrazine oxalate (40 g) in ethanol (100 ml) was heated at sufficient temperature and in a manner to allow removal of the ethanol by distillation. The temperature was gradually raised to about 130°, and heating was continued at this temperature for 4 hours, during which time by-product water and additional ethanol were continuously removed by distillation. The reaction mixture, after cooling to room temperature, was dissolved in methylene chloride and extracted with a saturated solution of sodium bicarbonate. The methylene chloride layer was dried and concentrated to give a viscous residue, which was induced to crystallize upon trituration with diethyl ether. The solid was collected to give 2-cyclohexyl-3-hydroxy-5-methylpyrazole (16.5 g), m.p. 153°. The assigned structure of the product as consistent with its infrared spectrum.

Provenance & Evidence