Benzyl Chloride → 3-Benzyloxypyridine

HRID 1590112Notes

Reaction equation

HRID 1590112 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[CH2:10]([O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 79713-HydroxypyridineHCID 14798Sodium Hydroxide

Product 1

HCID 100126353-Benzyloxypyridine

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-hydroxypyridine (24.7 g, 260 mmole) in distilled methylene chloride (260 ml) were added Adogen 464 (1.6 ml), 40% NaOH (130 ml), benzyl chloride (32 ml, 278 mmole), followed by stirring for 3 days at room temperature. The organic layer was separated from the reaction solution, and the aqueous layer was admixed with water and extracted with methylene chloride. The resulting extract was combined with the methylene chloride layer separated previously, and the combined solution was washed with saturated saline, dried over K2CO3 and freed of the solvent by distillation. The residue was purified on a column of silica gel (7734, n-hexane:ethyl acetate=20:1 to 5:1).

Workup

  1. customThe organic layer was separated from the reaction solution
  2. extractionextracted with methylene chloride
  3. extractionThe resulting extract
  4. customseparated previously
  5. washthe combined solution was washed with saturated saline
  6. dry with materialdried over K2CO3
  7. distillationfreed of the solvent by distillation
  8. customThe residue was purified on a column of silica gel (7734, n-hexane:ethyl acetate=20:1 to 5:1)

Sources & evidence

ORD record
ord-8b2fd9612f454c39a96504546bb3533e
Source dataset
uspto-grants-1993_04
Patent number
US05202334

Reaction notes

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