Hydrochloric Acid → Nicotinic acid, dodecyl ester

HRID 231495Notes

Reaction equation

HRID 231495 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[OH-].[Na+].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].Cl>CN(C)P(N(C)C)(N(C)C)=O>[C:1]([O:9][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 938Nicotinic AcidHCID 89191-BromododecaneHCID 14798Sodium Hydroxide

Product 1

HCID 251842Nicotinic acid, dodecyl esterYield 77.2%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

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.

Workup

  1. customat room temperature
  2. customfor 1 hour
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue was purified by column chromatography (Wakogel C-300, benzene:ethyl acetate=6:1 v/v)
  9. customrecrystallized from methyl alcohol at 1° C.

Sources & evidence

ORD record
ord-bf9661c0c7d946bab18ac2c2194303f4
Source dataset
uspto-grants-1989_07
Patent number
US04847260

Reaction notes

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