Nicotinic Acid → HCID 13773415, compound

HRID 231496Notes

Reaction equation

HRID 231496 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:14]([CH:16]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:17]O)[CH3:15].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.CN(C)C=O>[C:1]([O:9][CH2:17][CH:16]([CH2:14][CH3:15])[CH2:19][CH2:20][CH2:21][CH3:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 77202-EthylhexanolHCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 13773415HCID 13773415, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent

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.

Workup

  1. temperaturewas refluxed in an eggplant type flask for 3 hours
  2. customThe solvent was removed by distillation
  3. temperaturethe mixture was refluxed for 4 hours
  4. customThe benzene layer was separated
  5. washwashed successively with a saturated sodium bicarbonate aqueous solution, water
  6. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. distillationThe residue was purified by distillation under reduced pressure and column chromatography

Sources & evidence

ORD record
ord-f915ccf450c94dddb20c64ac46f42d06
Source dataset
uspto-grants-1989_07
Patent number
US04847260

Reaction notes

Loading…