Benzyl Alcohol → 2-(Benzyloxy)pyridine

HRID 1665625Notes

Reaction equation

HRID 1665625 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[CH2:8]([O:15][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 79772-ChloropyridineHCID 14797Potassium Hydroxide

Product 1

HCID 2958592-(Benzyloxy)pyridineYield 22.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

2-Chloro-pyridine (5 g, 44 mmol) was added to a stirred solution of benzylalcohol (6.1 g, 57.2 mmol), KOH (2.9 g, 52.8 mmol) and 18 crown[6] (50 mg) in toluene (20 mL) and the resulting mixture was heated to reflux at 110° C. for 6 hours. The reaction mixture was then cooled to room temperature and concentrated. The residue was diluted with waster and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 1.85 g (22%) of 2-benzyloxy-pyridine.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated
  4. additionThe residue was diluted with waster
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d50dc4916991487fb026bef14c67ba58
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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