Hydrochloric Acid → Nicotinic acid, dodecyl ester

Participants

Reaction Steps

In 100 ml of hexamethylphosphoramide was dissolved 4.9 g (0.04 mol) of nicotinic acid, and a 25% aqueous solution of sodium hydroxide (0.06 mol) was added thereto, followed by stirring using a magnetic stirrer at room temperature for 1 hour. To the mixture was further added 29.8 g (0.12 mol) of lauryl bromide, and the stirring was continued for an additional 24 hours. The reaction mixture was added to 200 ml of a 5% aqueous solution of hydrochloric acid and extracted with diethyl ether. The extract was washed with water, dried over sodium sulfate and distilled to remove the solvent. The residue was purified by column chromatography (Wakogel C-300, benzene:ethyl acetate=6:1 v/v) and recrystallized from methyl alcohol at 1° C. to obtain 9 g of n-dodecyl nicotinate as a colorless liquid in a yield of 77%, based on the nicotinic acid.

Provenance & Evidence