Benzyl Chloride → 5-(Benzyloxy)-2-methylpyridine

HRID 2049286Notes

Reaction equation

HRID 2049286 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[CH2:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydride

Product 1

HCID 123972515-(Benzyloxy)-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

The solution of 32.7 g of 2-methyl-5-hydroxy-pyridine in 300 ml of dimethylformamide is added to a suspension of 12.8 g of sodium hydride (57% mineral oil dispersion) in 150 ml of dimethylformamide, with stirring. Then the mixture is heated to 100° and maintained at 100° for 18 hours. After that, the mixture is cooled to room temperature and to the cooled mixture is added a solution of 49.8 g of benzyl chloride in 100 ml of dimethylformamide over a period of 30 minutes. The mixture is then refluxed for 7 hours, cooled and then evaporated to a residue. The residue is partitioned between water and ether, the layers are separated and the water layer extracted with ether. The ether layer is combined with ether extract, dried over sodium sulfate, filtered and the ethereal filtrate is distilled off. The residue is distilled to yield 5-benzyloxy-2-methyl-pyridine, boiling at 100°-102°/0.02 mm/Hg.

Workup

  1. temperatureThen the mixture is heated to 100°
  2. temperaturemaintained at 100° for 18 hours
  3. temperatureThe mixture is then refluxed for 7 hours
  4. temperaturecooled
  5. customevaporated to a residue
  6. customThe residue is partitioned between water and ether
  7. customthe layers are separated
  8. extractionthe water layer extracted with ether
  9. extractionextract
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. distillationthe ethereal filtrate is distilled off
  13. distillationThe residue is distilled

Sources & evidence

ORD record
ord-2fc6d9746fc94a8998e60f581b621040
Source dataset
uspto-grants-1980_04
Patent number
US04197302

Reaction notes

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