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

HRID 1606304Notes

Reaction equation

HRID 1606304 reaction equation
[O-]CC.[Na+].[Na].[OH:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH2:14]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 142752-Methyl-5-hydroxypyridineHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 123972515-(Benzyloxy)-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of sodium ethoxide prepared from 1.3 g. (0.0565 g. -atom) of sodium and 30 ml. of absolute ethanol is added a solution of 5-hydroxy-2-methylpyridine (5.0 g., 0.0458 mol) in 15 ml. of ethanol, followed by 8.6 g. (0.05 mol) of benzyl bromide. The mixture is refluxed for three hours, poured into 150 ml. of water and extracted with ether. The extract is dried and then treated with ethereal hydrogen chloride. The hydrochloride salt is dissolved in water and the aqueous solution is washed with ether, basified and extracted with ether. The dried extract is treated with charcoal and evaporated to give 5-benzyloxy-2-methylpyridine as a pale yellow oil.

Workup

  1. temperatureThe mixture is refluxed for three hours
  2. additionpoured into 150 ml
  3. extractionof water and extracted with ether
  4. customThe extract is dried
  5. additiontreated with ethereal hydrogen chloride
  6. dissolutionThe hydrochloride salt is dissolved in water
  7. washthe aqueous solution is washed with ether
  8. extractionextracted with ether
  9. extractionThe dried extract
  10. additionis treated with charcoal
  11. customevaporated

Sources & evidence

ORD record
ord-a866129016974d578463fa6cd8105d2a
Source dataset
uspto-grants-1976_04
Patent number
US03952101

Reaction notes

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