Hydrogen Bromide → Phenol, 4-(5-octyl-2-pyridinyl)-

HRID 3931Notes

Reaction equation

HRID 3931 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.Br.O>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 140699212-(4-Methoxyphenyl)-5-octylpyridine

Product 1

HCID 1725484Phenol, 4-(5-octyl-2-pyridinyl)-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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.

Workup

  1. temperaturethe solution was heated for 15 hours
  2. temperatureunder reflux
  3. extractionthe organic layer was extracted with chloroform
  4. washAfter washing the
  5. extractionextract three times with water
  6. customthe chloroform was removed by distillation
  7. customThe residue was recrystallized from a mixture of acetone and hexane

Sources & evidence

ORD record
ord-af619c8be0ee4e34923575da7dc53150
Source dataset
uspto-grants-1988_02
Patent number
US04723018

Reaction notes

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