Ethanol → 3-Octylpyridine

HRID 1607491Notes

Reaction equation

HRID 1607491 reaction equation
FC1C=C([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][N:10]=2)C=CC=1O.C(O)C.[OH-].[K+].CC(CC)CCCCBr>C1(C)C=CC=CC=1.O>[CH2:15]([C:12]1[CH:13]=[CH:14][CH:9]=[N:10][CH:11]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 2259235HCID 2259235, compoundHCID 132180865-Methylheptyl bromide

Product 1

HCID 5294073-OctylpyridineYield 134.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To this 2-(m-fluoro-p-hydroxyphenyl)-5-octylpyridine (2 g, 0.007 mol) were added ethanol (20 ml), KOH (0.4 g, 0.007 mol) and optically active 5-methylheptyl bromide (1.4 g, 0.007 mol), followed by heating the mixture under reflux with stirring for 4 hours, cooling, adding water and toluene, transferring the mixture into a separating funnel, washing the resulting organic layer with 2N-NaOH aqueous solution, washing with water, distilling off the solvent under reduced pressure and recrystallizing the residue in a freezer to obtain the objective optically active (S)-2-p-5-methyl-heptyloxy-m-fluorophenyl)-5-octylpyridine (1.8 g). This product had the following phase transition C-Sc *: 33.0° C., Sc *-SA : 33.5° C., SA -I: 39.4° C. Further, the elemental analysis values accorded well with its calculated values as follows:

Workup

  1. temperatureby heating the mixture
  2. temperatureunder reflux
  3. temperaturecooling
  4. washwashing the resulting organic layer with 2N-NaOH aqueous solution
  5. washwashing with water
  6. distillationdistilling off the solvent under reduced pressure
  7. customrecrystallizing the residue in a freezer

Sources & evidence

ORD record
ord-a735bb7351d645e1bc2da63dba02a91c
Source dataset
uspto-grants-1989_09
Patent number
US04865763

Reaction notes

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