Phenol → 2-Methyl-6-phenoxypyridine

HRID 1758972Notes

Reaction equation

HRID 1758972 reaction equation
Br[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>O.CCOCC>[O:15]([C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 792052-Bromo-6-methylpyridine

Product 1

HCID 129596942-Methyl-6-phenoxypyridineYield 124.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
210 °C

Procedure

A mixture containing 50.28 g of 6-bromo-2-picoline, 83.01 g of phenol and 120.86 g of potassium carbonate under an atmosphere of nitrogen was heated in an oil bath maintained at 210° C. for 20 hrs. After cooling to room temperature, the reaction mixture was dissolved in 1000 ml of H2O and 500 ml of ether. The layers were then separated and the aqueous layer extracted with ether. The combined etheral extracts were washed three times with 5% NaOH and then once with H2O. After drying the etheral layer over anhydrous Na2SO4, removal of the solvents afforded 67.3 g of an orange oil. Distillation afforded 44.32 g of colorless oil, b.p. 80°-85° at 5 mm.

Workup

  1. temperaturewas heated in an oil bath
  2. temperatureAfter cooling to room temperature
  3. customThe layers were then separated
  4. extractionthe aqueous layer extracted with ether
  5. washThe combined etheral extracts were washed three times with 5% NaOH
  6. customAfter drying the etheral layer
  7. customover anhydrous Na2SO4, removal of the solvents

Sources & evidence

ORD record
ord-b8011dbbea124097b0a7eba0c58f72f1
Source dataset
uspto-grants-1982_07
Patent number
US04338326

Reaction notes

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