Reaktion #351285

Reaktionsgleichung

hexadecanoic acid

monosodium

hydroxylamine hydrochloride

→

3-Dodecyl-5-isoxazole carboxylic acid

Lösungsmittel

acetic acid

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool
2. 2
   Sonstigepartitioned between H2O (250 mL) and chloroform (400 mL)
3. 3
   WaschenThe organic layer was washed (saturated NaCl)
4. 4
   Trocknendried (MgSO4)
5. 5
   workup.DISSOLUTIONThe residue was dissolved (toluene)
6. 6
   Sonstigethe solid recrystallized from toluene
7. 7
   Sonstigeto give a white solid, yield 5.62 g (43%), mp 119°-122° C.

Vorschrift

To a stirred, warm (55° C.) solution of hexadecanoic acid, 2,4-dioxo, ethyl ester, monosodium salt (15.50 g, 0.046 mol) in glacial acetic acid (125 mL) was added dropwise a solution of hydroxylamine hydrochloride (6.45 g, 0.093 mol) in water (32 mL) over 10 minutes, and the mixture was stirred at 60° C. for 25 hours. The mixture was allowed to cool and partitioned between H2O (250 mL) and chloroform (400 mL). The organic layer was washed (saturated NaCl), dried (MgSO4), and rotoevaporated. The residue was dissolved (toluene), rotoevaporated, and the solid recrystallized from toluene to give a white solid, yield 5.62 g (43%), mp 119°-122° C.

Quelle