Butyl bromide → HCID 19772698, compound

HRID 1788620Notes

Reaction equation

HRID 1788620 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][N:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].Br[CH2:20][CH2:21][CH2:22][CH3:23].[OH-].[K+]>C(O)C>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][N:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 19842034HCID 19842034, compound

Product 1

HCID 19772698HCID 19772698, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.8 g of the resulting 2-(p-pentylphenyl)-5-hydroxypyridine, 2 g of 1-bromobutane and 0.8 g of potassium hydroxide placed in 60 ml of ethanol were heated under reflux for 4 hours. The potassium bromide precipitated during the reaction was removed by filtration. The ethanol was removed by distillation. The residue was extracted with diethylether and the ether layer was washed with water several times and then the ether was removed by distillation. The residue was distilled under reduced pressure. The collected fraction having a boiling point of 185° to 187° C./2 mmHg was recrystallized from methanol to yield 1.7 g of 2-(p-pentylphenyl)-5-butyloxypyridine.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 4 hours
  3. customThe potassium bromide precipitated during the reaction
  4. customwas removed by filtration
  5. customThe ethanol was removed by distillation
  6. extractionThe residue was extracted with diethylether
  7. washthe ether layer was washed with water several times
  8. customthe ether was removed by distillation
  9. distillationThe residue was distilled under reduced pressure
  10. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-c2c91aacfc624edc84b39cb1c3b96db2
Source dataset
uspto-grants-1987_08
Patent number
US04684220

Reaction notes

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