Reaction #318678

Reaction equation

sodium bicarbonate

nicotinic acid

thionyl chloride

2-ethylhexyl alcohol

→

2-ethylhexyl nicotinate

Yield 70.0%

Solvents

benzene

dimethylformamide

benzene

Conditions

Workup

1. 1
   Temperaturewas refluxed in an eggplant type flask for 3 hours
2. 2
   OtherThe solvent was removed by distillation
3. 3
   Temperaturethe mixture was refluxed for 4 hours
4. 4
   OtherThe benzene layer was separated
5. 5
   Washwashed successively with a saturated sodium bicarbonate aqueous solution, water
6. 6
   Dryinga saturated sodium chloride aqueous solution, dried over sodium sulfate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   Otherto remove the solvent
9. 9
   workup.DISTILLATIONThe residue was purified by distillation under reduced pressure and column chromatography

Procedure

A mixture of 10 g of nicotinic acid (0.08 mol), 25 g of thionyl chloride (0.21 mol), 1.5 ml of dimethylformamide and 200 ml of benzene was refluxed in an eggplant type flask for 3 hours. The solvent was removed by distillation. To the residue were added 20.8 g (0.16 mol) of 2-ethylhexyl alcohol and benzene, and the mixture was refluxed for 4 hours. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate. The benzene layer was separated, washed successively with a saturated sodium bicarbonate aqueous solution, water and a saturated sodium chloride aqueous solution, dried over sodium sulfate and distilled to remove the solvent. The residue was purified by distillation under reduced pressure and column chromatography to obtain 9.1 g (70%) of 2-ethylhexyl nicotinate.

Source