Sodium Hydroxide → 3-(Pyridin-2-yl)phenol

HRID 539461Notes

Reaction equation

HRID 539461 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.Cl.N1C=CC=CC=1.[OH-].[Na+]>O>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27597152-(3-Methoxyphenyl)pyridineHCID 10176127Pyridinium chloride

Product 1

HCID 134170943-(Pyridin-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

To a 500 mL round bottom flask was added 2-(3-methoxyphenyl)pyridine (21.3 g, 115 mmol) and pyridine hydrochloride (107.5 g, 930 mmol). The reaction mixture was heated to 190° C. for 8 hours under nitrogen. The reaction mixture was cooled slightly and water was added. The mixture was stirred overnight. The pH of the solution was adjusted to 7 with 10% sodium hydroxide solution, extracted three times with dichloromethane. The organic layers were washed with 10% LiCl solution, brine, dried over magnesium sulfate, filtered, and evaporated. The residue was distilled on a Kugelrohr to remove the remaining pyridine (18 g, 91%).

Workup

  1. temperatureThe reaction mixture was cooled slightly
  2. extractionextracted three times with dichloromethane
  3. washThe organic layers were washed with 10% LiCl solution, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe residue was distilled on a Kugelrohr
  8. customto remove the remaining pyridine (18 g, 91%)

Sources & evidence

ORD record
ord-2a9fbd57e9614a1ebafd6cfa901ec6ea
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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