Benzyl Alcohol → 2,6-bis(benzyloxy)pyridine

HRID 1492372Notes

Reaction equation

HRID 1492372 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Cl)[N:11]=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 169892,6-DichloropyridineHCID 24758Sodium hydride

Product 1

HCID 8199362,6-bis(benzyloxy)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl alcohol (5.1 g; 0.05 mols) was reacted with 2,6-dichloropyridine (3.5 g; 0.024 mols) utilizing sodium hydride (1.2 g) and, as solvent, dimethylformamide by the procedure of Example 1 above. Usual work up, chromatography and recrystallisation gave 2,6-dibenzyloxypyridine as a colorless solid (5.5 g; 81%). Melting point: 74° C.

Workup

  1. customUsual work up, chromatography and recrystallisation

Sources & evidence

ORD record
ord-f9b3b78878424aa0a87f6d1f1d47ea93
Source dataset
uspto-grants-1994_12
Patent number
US05374604

Reaction notes

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