Benzyl Alcohol → 2-benzyloxy-5-nitro-pyridine

HRID 74611Notes

Reaction equation

HRID 74611 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[Na].[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH2:12]([O:19][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 783082-Chloro-5-nitropyridineHCID 5360545Sodium

Product 1

HCID 2956762-benzyloxy-5-nitro-pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

32 g (0.20 mol) 2-chloro-5-nitropyridine in 120 mL toluene were combined with 200 mL (0.20 mmol) of a 1M sodium benzylate solution in benzylalcohol and stirred overnight at RT. The organic phase was washed with water and saturated sodium chloride solution, dried on sodium sulphate and the toluene was eliminated by distillation. The residue was cooled with ice, the precipitate formed was suction filtered and washed several times with tert.-butylmethylether.

Workup

  1. washThe organic phase was washed with water and saturated sodium chloride solution
  2. customdried on sodium sulphate
  3. distillationthe toluene was eliminated by distillation
  4. temperatureThe residue was cooled with ice
  5. customthe precipitate formed
  6. filtrationfiltered
  7. washwashed several times with tert.-butylmethylether

Sources & evidence

ORD record
ord-d214f498422c427f90ac0c65a1d705e9
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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