Reacción #351285

Ecuación de reacción

hexadecanoic acid

monosodium

hydroxylamine hydrochloride

→

3-Dodecyl-5-isoxazole carboxylic acid

Disolventes

acetic acid

water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente