Reacción #4028

Ecuación de reacción

sodium hydroxide

2-(p-hydroxyphenyl)-5-octylpyridine

(R)-1-bromo-(4-methyl)decane

→

(R)2-[p-(4-methyldecyloxy)phenyl]-5-octylpyridine

Rendimiento 47.1%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting solution was heated to a temperature between about 90° and 100° C. for 3 hours
2. 2
   Extracciónthe organic layer was extracted with chloroform
3. 3
   LavadoAfter washing the
4. 4
   Extracciónextract three times with water, chloroform
5. 5
   Otrowas removed by distillation
6. 6
   OtroThe residue was chromatographed over 2.5×100 (cm) of silica gel
7. 7
   OtroThe effluent was repeatedly recrystallized from a mixture of methanol and acetone

Procedimiento

20 ml of a 30% aqueous solution of sodium hydroxide was added dropwise to a mixture of 2 g (0.007 mol) of 2-(p-hydroxyphenyl)-5-octylpyridine and 1.65 g (0.007 mol) of (R)-1-bromo-(4-methyl)decane with stirring. The resulting solution was heated to a temperature between about 90° and 100° C. for 3 hours. 150 ml of water was added to the reaction solution and the organic layer was extracted with chloroform. After washing the extract three times with water, chloroform was removed by distillation. The residue was chromatographed over 2.5×100 (cm) of silica gel and developed with hexane and benzene. The effluent was repeatedly recrystallized from a mixture of methanol and acetone to yield 1.44 g (0.0033 mol) of (R)2-[p-(4-methyldecyloxy)phenyl]-5-octylpyridine.

Fuente