Phenol → HCID 22456677, compound

HRID 2186479Notes

Reaction equation

HRID 2186479 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[O:7]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 22456677HCID 22456677, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of phenol (5.25 g, 55.8 mmol) and 2-chloromethylpyridine hydrochloride (10 g, 61.0 mmol) in 80 mL of toluene was added sodium hydroxide (5.35 g, 134 mmol. The mixture was refluxed for 16 hours. The mixture was washed twice with 60 mL of water. The organic layer was then extracted three times with 25 mL of 6 N HCl. The aqueous layer was made basic with 250 mL of 10% NaOH and extracted three times with 150 mL of CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound as a yellow oil (10.6 g, 94%). ES (+) MS m/e=186 (M+H).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. washThe mixture was washed twice with 60 mL of water
  3. extractionThe organic layer was then extracted three times with 25 mL of 6 N HCl
  4. extractionextracted three times with 150 mL of CH2Cl2
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45c827302e1c43be92007d0be03b2448
Source dataset
uspto-grants-2002_06
Patent number
US06403792B1

Reaction notes

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