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Nicotinic Acid → Iso-hexadecyl nicotinate

HRID 1650120
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1650120
[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 3

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

Produkt 1

HCID 23053586Iso-hexadecyl nicotinate

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  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%

Quellen und Nachweise

ORD-Eintrag
ord-86d72f3bdef140eab872014c8d7dc739
Quelldatensatz
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04923686

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