Palmitoyl chloride → Tert-butyl 3-hexadecanoyloxyoctadecanoate

HRID 236475

Reaktionsgleichung

Reaktionsgleichung von HRID 236475
[OH:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:26](Cl)(=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>N1C=CC=CC=1>[C:26]([O:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5])(=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Komponenten

4

Edukt 2

HCID 8206Palmitoyl chlorideHCID 13962663Tert-butyl 3-hydroxyoctadecanoate

Produkt 1

HCID 20216792Tert-butyl 3-hexadecanoyloxyoctadecanoateAusbeute 79,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To tert-butyl 3-hydroxyoctadecanoate (120 g) in pyridine (500 ml) was added palmitoyl chloride (120 g) at 0° C. The mixture was stirred at 0° C. for 5 hours and then allowed to stand over-night at room temperature. Pyridine was removed under reduced pressure and the residue was poured into water. The resulting mixture was stirred at ambient temperature for 2 hours, acidified with 1N HCl, extracted with ethyl acetate, and washed with water. Evaporation of the solvent gave a residue which was purified by silica gel column chromatography (30% CH2Cl2 --CCl4) to afford tert-butyl 3-hexadecanoyloxyoctadecanoate (160 g) as an oil.

Aufarbeitung

  1. waitto stand over-night at room temperature
  2. customPyridine was removed under reduced pressure
  3. additionthe residue was poured into water
  4. stirringThe resulting mixture was stirred at ambient temperature for 2 hours
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. customEvaporation of the solvent
  8. customgave a residue which
  9. customwas purified by silica gel column chromatography (30% CH2Cl2 --CCl4)

Quellen und Nachweise

ORD-Eintrag
ord-a1d605ae479d4d06a3230aeb9319610c
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04643990

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