Pyridine → 12-(Acryloyloxy)dodecanoic acid

HRID 1871827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1871827
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].N1C=CC=CC=1.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>O1CCCC1>[C:22]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])(=[O:25])[CH:23]=[CH2:24]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 13140Acryloyl chlorideHCID 7903412-Hydroxydodecanoic Acid

Produkt 1

HCID 2232822312-(Acryloyloxy)dodecanoic acidAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

12-Hydroxydodecanoic acid (5.0 g, 0.023 mol) dissolved in tetrahydrofuran (100 ml) and pyridine (2.16 g, 0.027 mol) was cooled to 0° C. Acryloyl chloride (3.15 g, 0.023 mol) in tetrahydrofuran (75 ml) was then added dropwise to the solution. The mixture was stirred for 5 hours at 0° C. then stirred overnight at room temperature. The precipitated pyridinium salt was filtered off and the solvent removed under vacuum. The resulting liquid was purified by flash chromatography (silica gel/chloroform) to give 2.5 g (40%) of the title compound. 1H NMR (60 MHz, CDCl3): δ 1.20 (s, 18H, CH2), 2.15 (m, 2H, CH2COOH), 4.0 (m, 2H, COOCH2), 5.7-6.0 (m, 3H, CH2 = and =CH).

Aufarbeitung

  1. stirringthen stirred overnight at room temperature
  2. filtrationThe precipitated pyridinium salt was filtered off
  3. customthe solvent removed under vacuum
  4. customThe resulting liquid was purified by flash chromatography (silica gel/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-1bded2c7cf87408497e48a59e01bd683
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06106806

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