Reaction #4027

Reaction equation

2-(p-methoxyphenyl)-5-octylpyridine

hydrobromic acid

water

→

2-(p-hydroxyphenyl)-5-octylpyridine

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperaturethe solution was heated for 15 hours
2. 2
   Temperatureunder reflux
3. 3
   Extractionthe organic layer was extracted with chloroform
4. 4
   WashAfter washing the
5. 5
   Extractionextract three times with water
6. 6
   Otherthe chloroform was removed by distillation
7. 7
   OtherThe residue was recrystallized from a mixture of acetone and hexane

Procedure

The 2-(p-methoxyphenyl)-5-octylpyridine was dissolved in 100 ml of acetic acid. 8 ml of 48% hydrobromic acid was added to the reaction solution and the solution was heated for 15 hours under reflux. 100 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, the chloroform was removed by distillation. The residue was recrystallized from a mixture of acetone and hexane to yield 8.3 g (0.029 mol) of 2-(p-hydroxyphenyl)-5-octylpyridine.

Source