Reacción #318677

Ecuación de reacción

lauryl bromide

nicotinic acid

sodium hydroxide

hydrochloric acid

→

n-dodecyl nicotinate

Rendimiento 77.2%

Disolventes

hexamethylphosphoramide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   Otrofor 1 hour
3. 3
   Extracciónextracted with diethyl ether
4. 4
   LavadoThe extract was washed with water
5. 5
   Secadodried over sodium sulfate
6. 6
   workup.DISTILLATIONdistilled
7. 7
   Otroto remove the solvent
8. 8
   OtroThe residue was purified by column chromatography (Wakogel C-300, benzene:ethyl acetate=6:1 v/v)
9. 9
   Otrorecrystallized from methyl alcohol at 1° C.

Procedimiento

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.

Fuente