Реакция #4028

Уравнение реакции

sodium hydroxide

2-(p-hydroxyphenyl)-5-octylpyridine

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

→

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

Выход 47.1%

Растворители

water

Условия реакции

Обработка

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

Методика

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.

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