Phenol → HCID 12899700, compound

Participants

Reaction Steps

A mixture of 46.0 g (0.3 m) of 3,4-dimethoxyphenol and 41.7 g (0.2 m) of 3-carbethoxy-4-piperidone HCl was cooled in an ice bath and treated with 100 cc of 73% v/v H2SO4 in 1/2 hr with stirring and protection from moisture. After stirring 4 days at room temperature the reaction was chilled and treated with an additional 24 g (0.156 m) of the phenol. After 5 days a second 24 g portion of the phenol was added. After stirring 6 days the reaction was treated with 150 g of ice and conc. NH4OH to pH 8-9. The resultant gum was stirred with 150 cc CHCl3 for 1/2 hr and was filtered. The filtrate was evaporated and the resultant gum was triturated with pet ether followed by ethyl ether. The resultant solid was crystallized from 150 cc 3 N HCl affording 33.4 g of the pyridin-5 -one as the hydrochloride, mp 254°-6° C.

Provenance & Evidence