Nicotinic Acid → Iso-hexadecyl nicotinate

HRID 2119210Notes

Reaction equation

HRID 2119210 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24].S(Cl)(Cl)=O>>[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH3:24])[CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 938Nicotinic AcidHCID 24386Thionyl ChlorideHCID 528326514-Methyl-1-pentadecanol

Product 1

HCID 23053586Iso-hexadecyl nicotinate

Conditions

Temperature
80 °C

Procedure

Iso-hexadecyl nicotinate was prepared from nicotinic acid and a commercial material, iso-hexadecyl alcohol, obtained from Farbwerke Hoechst AG. The general method of Example 1 was used except that the temperature after thionyl chloride addition was maintained at 80° C. for 2 hours, and after the esterification reaction the solution was cooled and washed with 0.5M sodium hydroxide, 0.5M hydrochloric acid and water. The solution was treated with activated carbon (2.5 % on the expected weight of product) at 50° C. for 1 hour, filtered and the solvent removed under reduced pressure. The light brown oil had an estimated purity of 93.4% and was distilled (boiling range 141°-146° C. at 0.03 mm mercury pressure) to provide a product of 99.8% estimated purity.

Workup

  1. customafter the esterification reaction the solution
  2. temperaturewas cooled
  3. washwashed with 0.5M sodium hydroxide, 0.5M hydrochloric acid and water
  4. additionThe solution was treated with activated carbon (2.5 % on the expected weight of product) at 50° C. for 1 hour
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. distillationwas distilled (boiling range 141°-146° C. at 0.03 mm mercury pressure)
  8. customto provide a product of 99.8%

Sources & evidence

ORD record
ord-c9a7f9644daf41f1a09845e4923845f7
Source dataset
uspto-grants-1987_07
Patent number
US04683310

Reaction notes

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