Ethanol → HCID 2861892, compound

HRID 2231162Notes

Reaction equation

HRID 2231162 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C(O)C.[OH-].[K+].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 702EthanolHCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 3999190HCID 3999190, compound

Product 1

HCID 2861892HCID 2861892, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-(m-Fluoro-p-hydroxyphenyl)-5-heptylpyridine (2 g, 0.007 mol), ethanol (20 ml), potassium hydroxide (0.48 g, 0.008 mol) and n-hexylbromide (1.4 g, 0.008 mol) were heated under reflux with stirring for 4 hours, followed by cooling the resulting reaction fluid, adding water and toluene, transferring the mixture into a separating funnel, washing the resulting organic layer with 2N-NaOH aqueous solution, then washing it with water, distilling off the solvent under reduced pressure, recrystallizing the residue from ethanol, filtering off it in a refrigerator and drying it to obtain the objective final product 2-(m-fluoro-p-hexyloxyphenyl)-5-heptylpyridine (1.7 g).

Workup

  1. temperatureunder reflux
  2. temperatureby cooling
  3. customthe resulting reaction fluid
  4. washwashing the resulting organic layer with 2N-NaOH aqueous solution
  5. washwashing it with water
  6. distillationdistilling off the solvent under reduced pressure
  7. customrecrystallizing the residue from ethanol
  8. filtrationfiltering off it in a refrigerator
  9. customdrying it

Sources & evidence

ORD record
ord-ca57ea1d4b35426f910ddd481d79385f
Source dataset
uspto-grants-1988_11
Patent number
US04781857

Reaction notes

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