Réaction #4028

Équation de réaction

sodium hydroxide

2-(p-hydroxyphenyl)-5-octylpyridine

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

→

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

Rendement 47.1%

Solvants

water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source