Toluene → 2-(5-Hydroxypentyloxy)pyridine

HRID 1005953Notes

Reaction equation

HRID 1005953 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-:8].[K+].C1[O:27][CH2:26][CH2:25]OCCOCCOCCOCCOC1.[C:28]1([CH3:34])C=CC=C[CH:29]=1>O>[OH:8][CH2:29][CH2:28][CH2:34][CH2:25][CH2:26][O:27][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 79772-ChloropyridineHCID 14797Potassium HydroxideHCID 2855718-Crown-6

Product 1

HCID 121371182-(5-Hydroxypentyloxy)pyridineYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.5 g of 1,5-pentadiol, 5.68 g of 2-chloropyridine, 5.6 g of KOH and 5.3 g of 18-crown-6-ether were added to 20 ml of toluene and the mixture was refluxed for 8 hours. After cooling, the reaction mixture was added with water and extracted with chloroform. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane) to obtain 6.5 g of the title compound (yield: 72%).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. dry with materialThe extract was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-383e6f3912b1434da7f83e964a6cd4bf
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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