Reaktion #468879

Reaktionsgleichung

hexadecanol

N-carbamylmaleimide

H2O

→

hexadecyl maleurate

Ausbeute 98.0%

Lösungsmittel

p-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated to reflux
2. 2
   FiltrationThe resulting solid was filtered
3. 3
   Waschenwashed with additional H2O
4. 4
   Sonstigedried

Vorschrift

A mixture of 49 g of hexadecanol (0.202 moles), 28 g of N-carbamylmaleimide (0.2 moles) and 270 mg of zinc chloride (0.002 moles) in 300 mL of p-dioxane was heated to reflux. After 24 hours, the mixture was cooled to room temperature and 200 mL of H2O was added. The resulting solid was filtered, washed with additional H2O and dried to afford 75 g (97% yield) of hexadecyl maleurate. M.P.: 106°-09° C. (dec.); 1H NMR (CDCl3): δ10.5 (br s, 1H), 8.2 (br s, 1H), 6.3 (m, 2H), 5.4 (br s, 1H), 4.2 (t, 2H), 1.6 (m, 2 H), 1.2 (m, 26H), 0.9 (t, 3H); HPLC (80% CH3CN/H2O, C18): Rt=6.9 minutes.

Quelle