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Nicotinic Acid → Iso-hexadecyl nicotinate

HRID 867619
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 867619
[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-e243b8aeb11e40868c3fc8c41e7e5e12
Quelldatensatz
uspto-grants-1988_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04775763

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